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Holiday Rentals with Pools in Windsor

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    Don't let other travellers get your favourite Windsor area holiday rental. You're so close to securing your perfect getaway. Book today.
    11 Matching Rentals in the Windsor AreaView all 73 rentals
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    The following rentals are within 15 kilometers of Windsor.
    Fallen Tree Ranch1 / 40
    (4)Excellent
    Sebastopol
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Black Mountain1 / 50
    (5)Excellent
    Forestville
    7 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    Healdsburg
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Charming Apartment in Dry Creek Valley, Healdsburg1 / 20
    (5)Excellent
    Healdsburg
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Satellite TV
    • Patio
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Mountain Views
    • DVD Player
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    We stayed here for nearly a week in July, and not only is it a relaxing home base for a wine country trip, but it is also a great location for the IM Santa Rosa race. It is...
    Reviewed 8 August 2017
    We enjoyed the place. Beautiful and peaceful location! The place is well stocked with cooking supplies and plenty of towels
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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...
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    Location Information
    Healdsburg, Sonoma County 95448
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Healdsburg
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Secure Parking
    • Satellite TV
    • Private Garden
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private and in the country near the Dry Creek and Russian River Valleys and yet only 10 minutes to the Healdsburg Plaza Square. Main house is 3BR/3BA and cottage is studio and full bath with plenty of outdoor furniture. NOTE: Pool heated in high season only. Enter through private gate and wind up a...
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    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Villa Aix Vineyards1 / 37
    (3)Excellent
    Healdsburg
    5 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Housekeeping Included
    • DVD Player
    • Mountain Views
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 January 2017
    We stayed at the Villa Aix Vineyards over New Year's. The villa is perfectly laid out for a party of twelve people (and one dog). The small vineyard is pleasant to walk in...
    Reviewed 11 April 2016
    We rented this house for my girlfriend's bachelorette weekend and it was absolutely beautiful! We were a large group but never left crowded as the house was very spacious...
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    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...
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    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 14
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    Sebastopol
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Housekeeping Included
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    YOU JUST FOUND YOUR HAVEN ON THE HILL.When folks come to visit, they never want to leave. This is why we created The Birdhouse. Now, it can be yours to enjoy. Located one hour north of San Francisco, smack-dab in the middle of the world famous Sonoma County wine country. We are 20 minutes...
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    Location Information
    Sebastopol, Sonoma County 95472
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Healdsburg
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Mountain Views
    • Patio
    • Private Garden
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cottage provides the true Dry Creek Valley wine country experience. with 270 degree views - from Mt. St. Helena in the east to the Pacific Coast Range in the west. Swim in the solar heated lap pool and then relax by the pool while soaking up the view. Walk through the vineyards and the rose...
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    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Healdsburg
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Wi-Fi
    • Private Garden
    • Satellite TV
    • Secure Parking
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Riverstone Ranch is truely a multi-family property. A location which caters to several generations with traditional main house, or modern 2BR/2BA "coup" or "Oak Tree House", each offers something a little different, all against gorgeous Russian River views and less than 5 minutes to downtown...
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    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    Healdsburg
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Washer
    • Satellite TV
    • Mountain Views
    • Children's Pool
    • Patio
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Healdsburg, Sonoma County 95492
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4BR/4BA hm w/solar htd pool surrounded by vineyard1 / 30
    (10)Excellent
    Healdsburg
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Internet Access
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Mountain Views
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    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...
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    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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