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Holiday Rentals in Healdsburg

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94 rentals in Healdsburg.
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Cabin In An Old Vine Zinfandel Vineyard. Dry Creek Valley. Five Miles To Plaza.
1 bedroom
1 bathroom
Sleeps 2
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Tanda Tula, Wine Country Sanctuary
5 bedrooms
3 bathrooms
Sleeps 12
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Healdsburg - Chalk Hill Wine Country Cottage
1 bedroom
1 bathroom
Sleeps 4
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Hilltop Hideaway: Bright, Fresh, Modern, Views And Only 2 Miles To Plaza
3 bedrooms
2 bathrooms
Sleeps 6
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Crossroads Vineyard: In the Heart of Healdsburg Wine Country
4 bedrooms
3 bathrooms
Sleeps 10
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Safe Retreat: Bicyclists, Birders, Wine Lovers, River Revelers Welcome!
3 bedrooms
2 bathrooms
Sleeps 8
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Healdsburg Cottage Walk to the Plaza, Workspace
1 bedroom
1 bathroom
Sleeps 4
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Secluded Valley Retreat
3 bedrooms
3 bathrooms
Sleeps 8
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Private Wine Country Retreat-Luxury estate, pool, hot tub, 3 miles to town
4 bedrooms
4 bathrooms
Sleeps 8
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Beautiful Mountain Top retreat less than 10 mins from downtown Healdsburg!
3 bedrooms
2 bathrooms
Sleeps 6
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Healdsburg River Front Oasis Retreat.
3 bedrooms
3 bathrooms
Sleeps 10
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Enjoy the Sunset from Upscale Home Among Vineyards — short walk to Healdsburg
2 bedrooms
2 bathrooms
Sleeps 4
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Modern country cottage: swimming pool, privacy, vineyard & 5 min. to Healdsburg
3 bedrooms
3 bathrooms
Sleeps 6
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Beautiful Studio Getaway in the Heart of Wine Country
1 bedroom
1 bathroom
Sleeps 2
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Wooded Restful Retreat, with broad scenic views, outdoor dining
2 bedrooms
2 bathrooms
Sleeps 4
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Secluded Luxury Vineyard Estate House and Guest House
5 bedrooms
4 bathrooms
Sleeps 4
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Healdsburg Villa on a Vineyard with Amazing Poolside Sunsets
4 bedrooms
3 bathrooms
Sleeps 8
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luxuriously appointed new large guest suite in a landmark Victorian
1 bedroom
1 bathroom
Sleeps 2
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Sunset Magazine Meets Healdsburg - Foodies & Wine Lovers
3 bedrooms
4 bathrooms
Sleeps 6
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Dry Creek Cottage - Healdsburg
1 bedroom
1 bathroom
Sleeps 4
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Beautiful Views! Dry Creek Valley Retreat with Deck & Pool, 5 min to Healdsburg
4 bedrooms
3 bathrooms
Sleeps 12
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Elegant - Peaceful - Romantic - Private
1 bedroom
1 bathroom
Sleeps 2
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Superb Healdsburg Location, Spectacular Views, Minutes to Town
4 bedrooms
3 bathrooms
Sleeps 7
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Dog Friendly Vineyard Estate Cottage with Lap Pool and Incredible Views
1 bedroom
1 bathroom
Sleeps 2
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Newly Listed 4BR/4.5BA Gorgeous 17 Acre Estate/Pool/Hot Tub/5 mins - Hburg Plaza
4 bedrooms
5 bathrooms
Sleeps 8
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Prime Dry Creek Location, Hot Tub, Bocce, Vineyard Views, 5 Minutes To Downtown
2 bedrooms
1 bathroom
Sleeps 6
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4,700 ft 4 bed & 4 bath ranch, 120 acres all to yourself with a lake and farm.
4 bedrooms
4 bathrooms
Sleeps 8
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Top Of The World Dry Creek Views With Hot Tub, POOL and new Tesla charger!
3 bedrooms
2 bathrooms
Sleeps 8
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Stunning, contemporary, eco-friendly home on 2.5 acres | Heated Pool & Spa
3 bedrooms
3 bathrooms
Sleeps 6
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Pet Friendly Wine Country Getaway On The Russian River Just 5 Minutes From Town
3 bedrooms
2 bathrooms
Sleeps 8
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Views, Hot Tub, Fireplace, Semi-Private Beach Close By , Pet-Friendly
3 bedrooms
2 bathrooms
Sleeps 8
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Updated cabin, right on Russian River, amazing views & location!
2 bedrooms
3 bathrooms
Sleeps 6
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Lovely Healdsburg Vineyard Home - 3br/2ba (up to 8 guests, children welcome)
3 bedrooms
2 bathrooms
Sleeps 8
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*New Home* 3 Blocks from Downtown Healdsburg Plaza!
2 bedrooms
2 bathrooms
Sleeps 6
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*LImited Time Discount* Healdsburg Riverside Cottage - Beautiful River Views
3 bedrooms
2 bathrooms
Sleeps 6
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Bunkhouse at Side Road Farm charming one bedroom cottage
1 bedroom
1 bathroom
Sleeps 2
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VineHaven- Spa, Gardens, & Spectacular Vineyard Views
3 bedrooms
2 bathrooms
Sleeps 8
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Updated Healdsburg River Cottage: Minutes from Plaza, Tasting Rooms & Vineyards
1 bedroom
1 bathroom
Sleeps 4
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Spectacular Two-Story Tuscan Villa Estate Home w/ Spa, Decks & Views
4 bedrooms
3 bathrooms
Sleeps 8
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Rendezvous Under the Oaks- Heated Pool & Spa available
3 bedrooms
3 bathrooms
Sleeps 8
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Stunning Mountain Top Estate with View Over Dry Creek Vineyards
4 bedrooms
5 bathrooms
Sleeps 8
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Vineyard Guest House
2 bedrooms
1 bathroom
Sleeps 4
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Creek Front Vineyard, West Dry Creek Healdsburg CA
6 bedrooms
7 bathrooms
Sleeps 12
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Luxury Wine Country Home in the Heart of Healdsburg with a Private Pool.
3 bedrooms
4 bathrooms
Sleeps 6
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Newly renovated & refurnished one-story 4br/3ba home, sleeps up to 8 guests
4 bedrooms
3 bathrooms
Sleeps 8
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Wine country getaway; stay in a winery
2 bedrooms
1 bathroom
Sleeps 4
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Wine Country Home on Chalk Hill - main house + pool house (up to 12 guests)
5 bedrooms
5 bathrooms
Sleeps 12
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Casa Chiquita - 3 Bedroom, 3 bath newly remodeled home with spa and pool
3 bedrooms
3 bathrooms
Sleeps 6
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Big Oak Vineyard / Vineyard Views, 3br/2ba, w.Spa and Attached to a Winery!
3 bedrooms
2 bathrooms
Sleeps 8
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VineHaven / Spa, Gardens, & Spectacular Vineyard Views
3 bedrooms
2 bathrooms
Sleeps 8
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