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Holiday Rentals and Homes in Healdsburg, CA

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    Travellers to Healdsburg are booking April dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 17
    5 of 5 stars (3) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    1 / 22
    5 of 5 stars (4) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    4 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    1 / 8
    5 of 5 stars (5) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    DEAR POTENTIAL GUEST: PLEASE CHECK CALENDAR BEFORE INQUIRING ABOUT AVAILABILITY - IT IS ALWAYS CURRENT. THANK YOU!! Since its opening in 2008, guest reviews confirm Dry Creek Villa to be a truly exceptional, idyllic retreat! We consistently rate 5/5 stars from prior guests. Among the various... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    5 of 5 stars Reviewed 1 August 2014
    My wife and I were looking for a quite, secluded retreat to totally unwind, we have found it. A modern, contemporary villa, on top of a ridge, with views in every direction. Only...
    5 of 5 stars Reviewed 25 April 2012
    This place was completely procured by my friend, Andrew, with the smallest of input from the other members of the party. We were all very impressed with the property, both in...
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    1 / 27
    5 of 5 stars (4) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • Waterfront
    • Hot Tub
    • Central Heating
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    About this property
    Nestled in a picturesque redwood grove on the banks of the Russian River, only 3 miles from historic Healdsburg Plaza, Redwood Tree House is one of the most enchanting vacation rental homes in all California Wine Country. The charming Main House and romantic 'La Casita' guest cottage provide a... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    5 of 5 stars Reviewed 13 September 2013
    I don't think I can say enough about how wonderful our trip to the Redwood Treehouse was! My husband and I were travelling with friends of ours, another couple, and this house was...
    5 of 5 stars Reviewed 11 July 2011
    We stayed in the Redwood Tree House for a long weekend in June. This home is very unique and a delight to stay in. You actually enter the home through a giant redwood tree and...
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    1 / 20
    5 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Waterfront
    • Sauna
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    About this property
    This distinctive and luxurious vacation home, with views and a private beach, offers 3 King Bedrooms, plus Queen guestrooms. The prime riverfront location in Healdsburg lies in the heart of Sonoma Wine Country, near the point where the Russian River flows through three world class wine growing... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    1 / 21
    5 of 5 stars (3) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    About this property
    Only 3.5 miles northeast of Healdsburg’s historic plaza, this stunning, nearly new, custom 3br + bonus room / 2.5 bath “castle” is a 4 acre vineyard estate property that is perched on a knoll and surrounded by vineyards with a beautiful view of the foothills of the Alexander Valley wine growing... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    5 of 5 stars Reviewed 31 March 2014
    Hummingbird Ridge is truly a little slice of heaven. The property sets on its own little vineyard with breathtaking views. The grounds are beautifully manicured with a wonderful...
    5 of 5 stars Reviewed 31 March 2014
    Amazing does not justify this beautiful home in wine country!! It is absolutely gorgeous! The property is well manained and has spectacular views. The house is very modern...
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    1 / 18
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Waterfront
    • Hot Tub
    • Internet Access
    • Outdoor Dining Area
    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
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    About this property
    This charming 3 bedroom, 2 bath home is one of four riverfront vacation homes offered by Wine Country Lodges, and has everything you need for a great Wine Country stay. It's located less than one mile from Healdsburg and all the excitement of a world class wine producing region, but feels world's... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    5 of 5 stars Reviewed 24 August 2015
    We loved staying at the Northwoods Lodge and would like to return again sometime. The property was very clean and well maintained, and the location, view, and river access are...
    4 of 5 stars Reviewed 19 November 2013
    First, I can say that the property was as described. Beautiful location with a great deck overlooking the Russian River. My complaint is that the property advertised both Cable...
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Private Outdoor...
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    • Mountain Views
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    • Patio
    • Washer
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    • Wheelchair access
    • Child-friendly
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    About this property
    Enjoy the beauty and lifestyle of Tuscany in Sonoma County. Set atop rolling hills among the vineyards, this exquisite estate has everything you could want—and then some. The good life is yours at this Dry Creek Valley paradise, located off a quiet country lane yet only a short drive to charming... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    1 / 20
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
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    About this property
    With a spectacular location on 12 beautifully landscaped and maintained acres, in the foothills between Santa Rosa and Healdsburg, Montebello Heights Estate is a newer Tuscan-themed, 4200 sq. ft. 4br/3.5ba, two-story home, with central heat and AC, and many custom features and special amenities,... View all property information
    Location Information
    Healdsburg, Sonoma County 95404
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    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Beautifully located, perched just above the Russian River, on S. Fitch Mountain, this Vintage 1927 river home has been beautifully renovated and modernized with central heat/AC, new dual-paned windows, high open-beamed ceilings, and all the modern conveniences while still maintaining its vintage... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    1 / 20
    5 of 5 stars (2) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Very well located on a ½ an acre with the back fence on the edge of Dry Creek Valley’s West Wines Vineyards, this beautiful ‘home away from home’ awaits you and your guests! First, be welcomed by a lovely landscaped yard out front with mature plantings and a small lawn which you can enjoy while... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    5 of 5 stars Reviewed 2 May 2014
    Maison du Soleil was perfect for our group of 8. We went away for a birthday trip and we all enjoyed the house immensely. Everything was immaculate, so much that we almost didn't...
    5 of 5 stars Reviewed 10 February 2014
    This property was perfect for our wine weekend getaway. Eight of us were very comfortable in this spacious, contemporary home. The house was clean and fully stocked which made it...
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    1 / 23
    4.5 of 5 stars (2) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Waterfront
    • Mountain Views
    • Internet Access
    • Satellite TV
    • Sauna
    • Central Heating
    • DVD Player
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Firefly Lodge is one of 4 luxurious riverfront vacation homes owned by Wine Country Lodges, located in beautiful natural settings in Sonoma Wine Country. (For information on all four visit the WineCountryLodges website.) Firefly Lodge is a warm and welcoming retreat, enjoying peaceful and... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    5 of 5 stars Reviewed 30 September 2014
    We had 8 people staying for a wedding in September in the Alexander Valley. The Firefly lodge was a perfect place to stay. It has a wonderful view of the Russion River. More...
    4 of 5 stars Reviewed 2 January 2013
    Wonderful place. I would suggest going when the weather is warmer so you can take advantage of the kayaks, hot tub and sauna. Beautiful home on the Russian River. Be prepared to...
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    1 / 28
    5 of 5 stars (13) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Washer
    • DVD Player
    • Waterfront
    • Wi-Fi
    • Mountain Views
    • Central Heating
    • Grill
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • Smoking allowed
    • Elder access
    • x
    About this property
    Our cottage is one of the best priced rentals right on the river with a big spa. It is priced the same or lower than other rentals across the street or up Fitch Mountain. There is a big difference being on the river, the large deck and dinning room have river views and lots of natural lights. The... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    5 of 5 stars Reviewed 30 June 2015
    We've wanted to stay on the Russian River for years and this cottage is the perfect spot! A quaint, unassuming place tucked away in the hills, under the towering redwoods, above...
    5 of 5 stars Reviewed 5 April 2015
    Easy breezy. Everything about this rental was a no-brainer. From communication with the owners to the accessibility and instructions to the quaintness and cleanliness of the...
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    1 / 23
    5 of 5 stars (3) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • Hot Tub
    • Air Conditioning
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    • Internet Access
    • Shared Outdoor Pool...
    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
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    About this property
    Very well located in Healdsburg, the ‘crown jewel’ of Sonoma County’s Wine Country, and under 2 miles from the historic Plaza, this 2000 sq. ft. vintage main house and 640 sq. ft. pool house, originally built in 1898 has many beautiful upgrades including central heat/AC, and combines the beautiful... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    5 of 5 stars Reviewed 9 October 2015
    Our group included three couples....perfect place to stay! The pool is great, very comfortable and clean throughout.
    5 of 5 stars Reviewed 28 November 2013
    Our group was thoroughly impressed with the amenities, location and of course home and land. It's nestled next to the vineyards and has one of the most amazing backyards I have...
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    1 / 28
    5 of 5 stars (6) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
    • Mountain Views
    • Satellite TV
    • Air Conditioning
    • Patio
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    This restored country home sits in the Alexander Valley near the famous Jimtown store, and looks across to and around vineyards. Just 7 minutes from Central Healdsburg, many wineries are nearby such as Fieldstone, White Oak, Sausal and Hanna, and Calistoga is within a 20 minute drive. As you drive... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    5 of 5 stars Reviewed 28 June 2015
    This house is adorable and just perfect for three couples for a long weekend. It's very well stocked and does not feel like a rental. The store is practically next door, and...
    5 of 5 stars Reviewed 24 July 2014
    We just celebrated a girls get togther at the Jimstown house and it was excellent. The house is in a great location, is artfully decorated and very comfortable. There were 4...
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    1 / 20
    5 of 5 stars (10) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Spectacular Two-Story Tuscan Villa Estate Home - 4br/3ba (2-8+ guests) w/ Spa, Decks & Views, on 5 Gated, Secluded Vineyard Acres. At the end of a private tree lined country lane, ‘under the Tuscan sun’, vacation in your ‘own private villa’. Nestled in charming, upscale, and historic... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    5 of 5 stars Reviewed 17 October 2015
    We loved our vacation in this luxury Tuscan villa. We chose this property for two reasons: we had three couples travelling and wanted three bedrooms/bathrooms that were comparable...
    5 of 5 stars Reviewed 30 September 2014
    I spent a week at the villa with my husband and two teenage girls. The house was perfect for us. There was plenty of room. The girls stayed on the upper level and we stayed...
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    1 / 37
    4.5 of 5 stars (4) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    All of the living at West Dry Creek View is at the back side of this beautiful modern minimalist country property. Three private acres offer a large in ground 22' x 60' swimming pool and large concrete hot tub amid gardens, emerald green lawn, and vineyard views galore, all less than ten minutes to... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    5 of 5 stars Reviewed 10 July 2015
    We absolutely loved our stay at this house! It was everything we wanted for the 4th of July weekend. The outdoor area/pool is to die for and the inside of the house looks like it...
    4 of 5 stars Reviewed 15 March 2015
    Beautiful location on west dry creek road making it convenient to get to many wineries and downtown Healdsburg but also secluded enough to get away from the hustle and bustle...
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    1 / 37
    5 of 5 stars (1) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • Housekeeping...
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    • x
    About this property
    Inspired by the Villa Gallici in Aix-en-Provence, Villa Aix Vineyards combines traditional, French cottage warmth with fresh, contemporary farmhouse flair.Nestled on a serene 20-acre vineyard in the Alexander Valley appellation of Sonoma's gorgeous rolling hills, this private estate offers all the... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    5 of 5 stars Reviewed 16 July 2015
    Villa Aix Vineyards is an amazing place to stay for a vacation. Surrounded by vineyards, it is a destination by itself. We spent a weekend here with 4 families and half of our...
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • Central Heating
    • Waterfront
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    • Pet-friendly
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    About this property
    Healdsburg Hideaway A Favorite Wine Country Getaway on The Russian River in Healdsburg Down a quiet lane lined with towering redwood trees lies the Hideaway, a fantastic Wine Country getaway that is just steps from the Russian river, yet only two miles from the historic, upscale and charming... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Balcony
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    About this property
    Buena Vista – beautiful view in Spanish.  When you reserve this 2400 square foot, 4 bedroom, 3 bath home, beautiful, panoramic views are just one of the many amenities you will be able to enjoy. The Buena Vista is an inviting and spacious home that accommodates up to eight guests. Whether you're... View all property information
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    Healdsburg, Sonoma County 95448
    1 / 24
    5 of 5 stars (1) Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Nestled on 10 acres in the prestigious Chalk Hill appellation of the Alexander Valley, this rustic, beautifully renovated and newly furnished, 5br/3.5ba, 3200 sq. ft., two-story lovely home with central heat/AC, sits on a wooded knoll just above the vineyards. There is a separate pool house on the... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    5 of 5 stars Reviewed 28 June 2013
    We stayed at this property for a girls weekend (my bachelorette trip, to be exact.) It was perfect! Exactly what we were looking for - which was plenty of space for 12 adults, a...
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Ideally located on 6 acres with a 2-acre Zinfandel vineyard, overlooking the West Dry Creek, this gated Estate sits atop a small hill with incredible panoramic views of the W. Dry Creek Valley and Mount St. Helena. This lovely ‘lady among the vines’ is spacious at 2500 sq. ft. with central... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    1 / 23
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Grill
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    About this property
    This beautiful retreat is in the heart of Russian River Valley. Relax on the patio adjacent to the seasonal creek among the vintage oaks and look out to 55 acres of vineyards and the Russian River. Situated on a Wine Road, this lovely get-a-way neighbors Thomas George Winery and Porter Creek with... View all property information
    Location Information
    Healdsburg, Sonoma County
    1 / 20
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Very well located, just a couple miles north of the charming, historic, upscale Healdsburg Plaza, is your wonderful Getaway with close access to the Hwy 101. This special home rests at the ‘gateway’ of the famed Dry Creek Valley wine growing region, with dozens of world class wineries, and tasting... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Outdoor Dining Area
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    • Satellite TV
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    • Pet-friendly
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    About this property
    Response time is typically within the hour except if making a request after 9pm pst which could be a few hours. This is a great chance to stay in a very comfortable and well decorated Sonoma style home just minutes from the beautiful town of Healdsburg and Windsor. If you don't head into... View all property information
    Location Information
    Healdsburg, Sonoma County 95492
    1 / 20
    4.5 of 5 stars (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Newly Renovated Healdsburg VineHaven - 3br/2ba (up to 8 guests, children welcome, small lapdogs considered) w/ Spa, Gardens, & Spectacular Vineyard Views Very well located at the north end of Healdsburg and the beginning of the famed Dry Creek Valley and vineyards, this newly renovated 50’s... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    5 of 5 stars Reviewed 13 August 2014
    Location could not have been better. The house and property were well done and very clean. Had everything we needed and more. Only one little thing we didn't like was the...
    4 of 5 stars Reviewed 21 June 2012
    We just returned from a long weekend trip to Russian River Valley for a wine tasting trip & 50th birthday celebration. I found VineHaven online while looking for a house rental...
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    1 / 20
    5 of 5 stars (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
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    • Hot Tub
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    • Pet-friendly
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    • Child-friendly
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    About this property
    **Special Rules With This House—NO EXCEPTIONS: No more than 4 cars may be on the property--ever. No more than 6 adults may occupy the property. Quiet time starts, and outside activities must end, at 9:00 P.M. No recreational vehicles Perfectly located only 3 miles from the charming and... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    5 of 5 stars Reviewed 9 September 2013
    We rented Limerick Lane in august & were thrilled with whole experience! You never know how on line house rental will go & this experience, happily, exceeded our expectations. It...
    5 of 5 stars Reviewed 15 August 2013
    880 Limerick Lane was beautiful, charming, clean and perfectly appointed! The kitchen-living room space was perfect for gathering the family and enjoying shared time. The...
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    1 / 17
    3.5 of 5 stars (3) Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    ENJOY...a fabulous vacation with old man river, at the RiverHouse, where the Redwoods meet the Russian River. With direct river access and its own private beach, this very special riverfront home is located just minutes from downtown Healdsburg, yet a world away, nestled on a wooded knoll on... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    5 of 5 stars Reviewed 28 June 2013
    Wonderful vacation home - not cabin, home. All amenities as advertised. Great bedrooms, bathrooms and kitchen. But the best part is outside. River at your back door, deck...
    5 of 5 stars Reviewed 12 July 2011
    We stayed at the Riverhouse over the July 4th weekend and couldn't have had a better time. The location is great, just a 10 minute drive from the center of Healdsburg but feels...
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Sauna
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    About this property
    Nestled between the Russian River, Alexander Valley, and Dry Creek Valley. Wine regions, the hotel is just minutes away from over 150 world renowned wineries, dining, arts, culture and outdoor activities. Attractions nearby a lso include the Healdsburg Center for the Arts, River Rock Casino,... View all property information
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    Healdsburg, Sonoma County 95448
    1 / 28
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Our home is a perfect starting point to Alexander Valley and Dry Creek wineries and a short walk to the banks of Russian River where you can float, kayak, paddle board or just lay in the sun. Nested on Fitch Mountain, our home is in the heart of nature. You are close enough to downtown... View all property information
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    Healdsburg, Sonoma County 95448
    5 of 5 stars Reviewed 9 June 2015
    I would definitely recommend this property. My wife and I stayed there with friends for a wine country holiday. The house seems recently remodeled with many seating areas both...
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    1 / 19
    5 of 5 stars (15) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Mountain Views
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    • Pet-friendly
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    About this property
    Enjoy the serene quiet of our rural setting just minutes from beautiful downtown Healdsburg. We are surrounded by vineyards,and the cottagey sits amidst a large organic flower and vegetable garden filled with butterflies, birds, and bees. Your private patio overlooks the Russian River Valley and... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    5 of 5 stars Reviewed 27 July 2015
    My wife and I stayed here for three nights with our young adult daughter on her first trip to the "wine country." We toured the Dry Creek Valley wineries one day and the Russian...
    5 of 5 stars Reviewed 16 April 2015
    We stayed over Thanksgiving 2014 and it was a perfect space for me, my husband and our 3 young children. Much more room and much more cost effective than any bed & breakfast, and...
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This Mediterranean home has casual elegance with expansive decks, patios, spa and a SOLAR HEATED SWIMMING POOL surrounded by flagstone and plenty of outdoor seating. The 4 bedrooms are all Kings, quite secluded both from each other and the common living spaces. All suites have private full... View all property information
    Location Information
    Healdsburg, Sonoma County 95436
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Children's Pool
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    About this property
    Situated on 2.5 acres, just minutes from the quaint downtown of Windsor and about 10 minutes from the Healdsburg square, Woody Creek Retreat is at the pinnacle of convenience while offering the serenity of a quiet country luxury farmhouse. Ideal for families, couples, or friends wanting a to... View all property information
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    Healdsburg, Sonoma County 95492
    1 / 29
    4 of 5 stars (2) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
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    • Internet Access
    • Waterfront
    • Satellite TV
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    • Pet-friendly
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    About this property
    This 3 story, 3+ bedroom classic river retreat has beautiful river views, and it's own dock. It is only a mile from Healdsburg and guests can take an easy and enjoyable walk to the Plaza, around which all the excitement and activity revolve in this picturesque, world class wine growing region.... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    4 of 5 stars Reviewed 22 August 2015
    The house (Old River Lodge) is beautiful and comfortable, but the parking is a bit tricky. The only real problem was major construction going on next door. The loud hammering...
    4 of 5 stars Reviewed 14 July 2014
    Spent a week at the Old River Lodge with both daughters and their husbands and had a most enjoyable time. The lodge is a three story home on the bank of the Russian River, with...
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    5 of 5 stars (2) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    This beautiful Healdsburg Estate home, located 3.5 miles southeast of the Downtown Plaza is a 3800 sq. ft. two-story custom home with central heat/AC, 4 bedrooms and a private sunroom with a convertible queen sofa making the 5th bedroom (combining to sleep 10), 3 beautiful full baths and 1 half... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    5 of 5 stars Reviewed 1 October 2014
    My husband and I spent an absolutely lovely week with friends at the Eastside Estate in August. The location is perfect: you're literally tucked away in the middle of a vineyard...
    5 of 5 stars Reviewed 28 September 2014
    We stayed at this wonderful property for 5 days with friends and family. The house has all the bells and whistles you could have on your dream wishlist for a vacation rental in...
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
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    • Terrace
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    • Pet-friendly
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    About this property
    The Space The perfect home away from home. Makes this your personal sanctuary wether you are staying for the weekend or for the whole month while looking for the perfect home to buy. Well appointed, decorated with international contemporary art with just enough touches that take you beyond the... View all property information
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    Healdsburg, Sonoma County 95448
    1 / 30
    5 of 5 stars (16) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Patio
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    • Outdoor Dining Area
    • Mountain Views
    • Grill
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    • Satellite TV
    • Shared Garden
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    • Pet-friendly
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    • ?
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    • x
    About this property
    Isabelle's Maison Zinscape’s Private Cottage and Garden Room are set among the Dry Creek Valley , with over 60 wineries and vineyards in the heart of the wine country. You pull down driveway to the doors of both seperate rooms which are adjacent to each other. You can come and go in privacy. The... View all property information
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    Healdsburg, Sonoma County 95448
    5 of 5 stars Reviewed 19 September 2015
    We rented the cottage and our friends stayed in the garden room. Both rooms were quite lovely and all that we expected. The location was convenient yet very private and quiet...
    5 of 5 stars Reviewed 1 December 2014
    This was perfect! So peaceful and beautiful, walking every morning, comfy bed, awesome food, off the hook wine and such a nice proprietor , BRUCE!
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Pet-friendly
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    About this property
    Our apt. is nestled in the heart of the gorgeous Dry Creek Valley wine country, 10 minutes away from Healdsburg and its many wineries, acclaimed restaurants, and shops galore. the apt. is 1150 Sq ft with 2 bedrooms, kitchen/great room, and deck/BBQ. We have 8 acres with organic gardens, raised... View all property information
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    Healdsburg, Sonoma County 95448
    1 / 20
    4.5 of 5 stars (4) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Washer
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    • Pet-friendly
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    About this property
    Enjoy the best of two worlds, the peace and tranquility of ‘country living’ among the vineyards and wineries of the Russian River Valley, and the convenience of being only five minutes from the historic Healdsburg’s Plaza. BellaGia Healdsburg is an upscale, and modern appointed three bedroom, three... View all property information
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    Healdsburg, Sonoma County 95448
    3 of 5 stars Reviewed 10 September 2014
    I was staying at Bella Gia with my husband and a few friends. We were in Healdsburg for our friends' wedding. The house is in an extremely convenient location to downtown...
    5 of 5 stars Reviewed 10 February 2014
    We had a wonderful time at BellaGia! The kitchen was very well equipped and perfect for cooking gourmet meals. The bedrooms and bathrooms were also perfect--especially for us...
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    4.5 of 5 stars (7) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Outdoor Dining Area
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    • Mountain Views
    • Grill
    • Satellite TV
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    • Shared Garden
    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Elder access
    • x
    About this property
    Location! Location! Location! Enjoy this newly renovated 2 bedroom, 2 full bath cottage with gourmet kitchen, wood burning fireplace, large back deck with vineyard views and more. Located 5 miles outside historic Healdsburg, just 90 minutes north of San Francisco and in the heart of Dry Creek... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    3 of 5 stars Reviewed 1 July 2015
    We loved the First Crush cottage. Very quaint, great location near the vineyards, clean etc. The only issues we had is that even though it is in a cool location, there wasn't...
    5 of 5 stars Reviewed 24 November 2013
    Comfortable, elegant, dining under by stars, looking at the vineyards -- perfect!
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Surrounded by trees and greenery, this top-quality retreat offers privacy as well as views of gently sloping mountains and plenty of fresh air. With a country setting but only a short five-minute drive to the center of charming downtown Healdsburg, this is truly the best of both worlds. Newly... View all property information
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    Healdsburg, Sonoma County 95448
    1 / 30
    5 of 5 stars (10) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Internet Access
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    • Private Outdoor...
    • Waterfront
    • Mountain Views
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    • Pet-friendly
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    • ?
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    • Elder access
    • x
    About this property
    'Mona, a name given to house by our daughter when she could not say 'Sonoma,' is a four bedroom/four bath, completely remodeled home including a one bedroom/one bath guest house in the heart of Dry Creek Valley in Healdsburg, California. Our vacation home sits on one acre nestled among the vines... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    5 of 5 stars Reviewed 14 September 2015
    Mona was just as warm & welcoming as the photos showcased. Celebrating our Mother's 90th, it was the perfect location to enjoy time together as family- plenty of games to enjoy...
    5 of 5 stars Reviewed 1 April 2015
    We rented this home for a group of nine former college roommates gathering for a long wine country weekend. Being unfamiliar with the area, we could not have lucked out more on...
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    1 / 21
    5 of 5 stars (25) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
    • Central Heating
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    • Balcony
    • Satellite TV
    • Patio
    • Wi-Fi
    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    Affordable Wine Country Home (up to 6 guests) and Country Cottage( for two guests) surrounded by 15 acres of vineyards. Both vacation homes are in private locations on one 15 acre gated estate. Location is everything! In Healdsburg everyone wants to be near the Plaza--we are just 1 & 1/2 miles... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    5 of 5 stars Reviewed 19 August 2014
    We enjoyed our stay in the farm house. It was a beautiful spot, we were surrounded by vineyards. The picture is a bit misleading, it was taken from a spot on top of a hill so...
    4 of 5 stars Reviewed 29 July 2014
    We can't say enough about the beautiful location of the house, just spectacular! The house was clean and everything you needed was provided, so from that standpoint, 10 out of 10...
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    3 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Porch
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    • Pet-friendly
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    About this property
    2nd floor: 11 foot ceilings. Beautiful, gourmet kitchen with stunning views. Kitchen is equipped with a Thermador 6 burner (and grill) gas stove top and double electric oven. Butcher block counter tops. Dishwasher, Professional quality knives and cookware. Large microwave. Spacious walk-in pantry.... View all property information
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    Healdsburg, Sonoma County 95448
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Patio
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    • x
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    About this property
    Spend your vacation in the heart of Healdsburg, CA at the Moorish-inspired Cypress House. Beautiful tiles, an interior courtyard, and an incredible view of downtown and beyond from the top floor terrace make this property unique to wine country. Located at the edge of a small shopping center, it... View all property information
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    Healdsburg, Sonoma County 95448
    1 / 10
    5 of 5 stars (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Patio
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    • Pet-friendly
    • Wheelchair access
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    • x
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    About this property
    Very conveniently located at the beginning of Dry Creek Road and minutes from downtown Healdsburg. Children welcome and pets considered. The house is a newly updated 1950's ranch house that has been tastefully and simply decorated. As you walk up the redwood porch and into the house, you enter... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    5 of 5 stars Reviewed 19 December 2014
    This house is tucked away on a tree lined street within Dry Creek Valley. It is a stone's throw from both Healdsburg and the Valley's Wineries which is a valuable asset as a...
    5 of 5 stars Reviewed 18 September 2014
    We are 5 women who meet several times a year for Wine Tasting Weekends, where cooking, relaxing and wine tasting are the focus. This is our 5th house rental in this area and is...
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    3.5 of 5 stars (7) Average
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Pet-friendly
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    • Child-friendly
    • ?
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    About this property
    This lovely little cottage is really a unique and hard to find category for a few guests or 2 couples. Furnished smartly, and priced right, this cottage offers big amenities for the vacation home traveler. Set on one acre, there is off street parking through gates, a hobby vineyard, and outdoor... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    5 of 5 stars Reviewed 26 May 2015
    Communication with owners was quick and easy. The place is close enough to town to walk. If you want to wake up and see vines, you won't be disappointed. Beads were super comfy...
    3 of 5 stars Reviewed 17 April 2014
    The home itself was great, and in the end we were able to get the keys to the place with no difficulty. However, my communications from the rental agency were unclear, and my...
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    1 / 21
    5 of 5 stars (17) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    About this property
    The elegant main home is a 4br/3ba, nearly 4000 sq. ft., two-story, gated estate with central heat/AC, a spectacular gourmet kitchen, abundant high end architectural details and custom finishes, fine furnishings, and the entire home is floored in honed hickory hardwood made even more comfortable... View all property information
    Location Information
    Healdsburg, Sonoma County 95492
    5 of 5 stars Reviewed 14 July 2014
    I am absolutely in love with Tertulia. We visited here for a friend's 50th birthday and had the time of our lives. The house is spacious, clean and thoughtfully appointed...
    5 of 5 stars Reviewed 4 June 2014
    Tertulia is the ideal vacation home for a wine country getaway with friends or family. My husband and I spent 4 days with friends and we loved every minute. The house has four...
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    1 / 26
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Enjoy the beauty of Healdsburg from the middle of a 12-acre vineyard at this three-bedroom vacation cottage, where you'll have your very own scenic deck and enclosed yard! Gorgeously situated just three miles from central Healdsburg in the heart of California wine country, this bright and... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    Healdsburg Vacation Rentals

    Beautiful Northern California has many fabulous destinations, and the town of Healdsburg in Sonoma County is at the top of the list. And if you are looking for a vacation rental in this slice of world famous wine country, we’ve got you covered. We have a huge variety of Healdsburg vacation rental listings. You might be looking for a large house for the whole family, or a quaint cottage for a special romantic getaway. Whatever your needs and budget, we can help you find the perfect vacation rental that will make your stay in Healdsburg even more amazing. We can also provide you with helpful user reviews of vacation rentals in Healdsburg and the surrounding area, so you’ll be sure to get good value for your money.

    Healdsburg a Slice of Paradise

    Small town charm, beautiful landscapes and outstanding weather are just a few of the trademark qualities that make Healdsburg so popular. Healdsburg combines five-star cuisine, rolling hills and world-acclaimed wine growing appellations for an experience you will never forget. When it’s time to relax at the end of the day, why stay in a cramped hotel when you can enjoy the comforts of home in one of our rental cottages, houses or cabins?

    Lots of Activities

    If you love the vibrant outdoors and colorful festivals, you will love Healdsburg. In April, you can help harvest roses and distill them into fragrant rose oil and rosewater as part of the Classic Perfume Rose Harvest & Distillation Tours. An annual sea food dinner at the Healdsburg Fire Department is also in April. From February to June, enjoy the "Russian River Good Old Days" exhibit at the Healdsburg Museum. And on the first Friday of the month, Williamson Wines sponsors an Epicurean Dinner at the Dry Creek Kitchen at Hotel Healdsburg.

    Food, Wine and Fun

    Speaking of eating, you won’t want to miss the chance to dine at Healdsburg’s amazing restaurants, including Affronti, Agave Mexican Restaurant &Tequila Bar, Thai Orchid Cuisine, Willi's Seafood & Raw Bar and Zin Restaurant & Wine Bar. And don’t forget to visit the beautiful wine country all around you, featuring names like Alexander Valley, Chalk Hill, Dry Creek Valley, and Russian River Valley. We’re here to help you make the most of your visit to Healdsburg. Let us help you find the perfect cozy cottage, cabin or house to make your stay in Healdsburg one you will always remember.