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Holiday Rentals with Pools in Windsor

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    $1,244 Average
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    Travellers to Windsor are booking April dates now. Secure your holiday rental today, and have the perfect trip.
    15 Matching Rentals in the Windsor AreaView all 51 rentals
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    The following rentals are within 10 kilometres of Windsor.
    Charming Apartment in Dry Creek Valley, Healdsburg1 / 40
    (5)Excellent
    Healdsburg
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Healdsburg
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Healdsburg
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Limerick Lane - Stunning, quiet, contemporary, single-level, eco-friendly home1 / 25
    (3)Excellent
    Healdsburg
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 October 2016
    the house is fabulous and the location is perfect.minutes to town and lots of wineriespeaceful setting and cool clean house
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    About this property
    Location, location location! Perfectly situated only 3 miles (a 5-7 minute drive) from the charming and historic Healdsburg Plaza, this fabulous, custom three-bedroom home abounds with special eco-friendly features. You will be wowed by this modern home’s beautiful open-beamed cathedral ceiling,...
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    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Healdsburg
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Washer
    • Parking
    • Hot Tub
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning gated modern ranch house is nestled on one acre among the vineyards, and very well located at the north end of Healdsburg on Alexander Valley Road. Just remodeled, professionally decorated and furnished, this single story, 2000 sq. ft., 3 bedroom, 2.5 bath home sits under the shade of...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Healdsburg
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Cable/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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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    EastSide - Newly renovated 2-story custom Estate - 5br+/3.5ba home, sleeps 101 / 25
    (2)Excellent
    Healdsburg
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Washer
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Hot Tub
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Very well located about 3.5 miles southeast of Healdsburg’s famed Plaza, the lovely Eastside Estate sits on 2+ beautifully manicured and wooded acres among the vineyards of the Russian River Valley appellation. Newly renovated, and professionally decorated and furnished, this Estate is nothing...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Bella Terra Healdsburg - Upscale, Modern four bedroom, three bath home1 / 20
    (5)Very good
    Healdsburg
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Grill
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 August 2016
    I rented this house with a group of 7 and it was PERFECT! The property is secluded, the pool is amazing and the beds are comfortable. The location is removed from Santa Rosa...
    Reviewed 11 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...
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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. Bella Terra Healdsburg is an upscale, and modern appointed four bedroom,...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Tertulia at Amber Ridge - Stunning Wine Country Gated Estate with pool & spa1 / 24
    (22)Excellent
    Healdsburg
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Grill
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Washer
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 November 2016
    Tertulia at Amber Ridge brings the best of wine country into one location. The house is spacious for multiple families with dining options to include 20 friends. Every morning...
    Reviewed 10 November 2016
    We recently stayed at Tertulia with 4 other couples while on a tour of the wine country. Tertulia was AMAZING! The house was beautiful and the grounds and amenities were...
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    About this property
    Tertulia at Amber Ridge – where good friends and family gather in stunningly beautiful, peaceful surroundings to enjoy each other’s company over great food and wine. Deep relaxation, pleasant conversation, laughter and joy ensue! Tertulia is a fabulous two-acre Wine Country sanctuary surrounded on...
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    Healdsburg, Sonoma County 95492
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Healdsburg
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Parking
    • Hot Tub
    • Air Conditioning
    • Grill
    • Internet Access
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ideally located on 7 hillside acres, in the famed Dry Creek Valley, this absolutely stunning, new, modern Wine Country home is a spectacular retreat nestled in Mother Nature’s paradise, with forever easterly views of the Dry Creek Valley. This magnificent architectural marvel was designed by John...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Chalk Hill Country Home - Wine Country Home - main house + pool house1 / 29
    (4)Very good
    Healdsburg
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Grill
    • Parking
    • Washer
    • Hot Tub
    • DVD Player
    • Internet Access
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 July 2016
    I loved it and I'd love to come back again. I love Sonoma County.The rooms were very comfortable. I just adored the pool. The weather was perfect. I can't wait til next year.
    Reviewed 11 July 2016
    This is a wonderful house for groups. The common space offers many seats. The hot tub is large enough for 7 people. There is a BBQ and lots of outdoor seating for families to...
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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. A separate pool house on the opposite...
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    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 5 Bedrooms, 4 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
    • Cable/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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    Healdsburg, Sonoma County 95492
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Healdsburg
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Hot Tub
    • Parking
    • Private Outdoor Pool (Unheated)
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sweeping vistas of the Alexander Valley are just one of the highlights at this gorgeous Healdsburg studio cottage for four. Part of a private and gated estate surrounded by rolling hills, your cottage includes a shared patio and outdoor grilling area. The cottage is stylishly appointed with art...
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    Healdsburg, Sonoma County 95448
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Healdsburg
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Grill
    • Hot Tub
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy an exceptional wine country getaway at this show-stopping gated 3BR/2.5BA Healdsburg estate with impressive amenities and sweeping Alexander Valley views. Designed by the homeowner (who is a renowned local architect), the property seamlessly pairs old-world charm with 21st-century luxuries....
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    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Healdsburg
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You’ve found a real gem with this hilltop studio cottage in Healdsburg, complete with walls of glass that open to stunning views across the Alexander Valley. Guests have shared access to a lovely al fresco dining and grilling area. The cottage is beautifully furnished with a well-stocked...
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    Location Information
    Healdsburg, Sonoma County 95448
    Condo/Apartment - 1 Bathroom, Sleeps 2
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