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Windsor Holiday Rentals with Pools

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    Travellers to Windsor are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    20 Matching Rentals in the Windsor AreaView all 59 rentals
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    Windsor
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Windsor
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Windsor
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    The following rentals are within 10 kilometres of Windsor.
    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
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Mountain Views
    • DVD Player
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 September 2017
    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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    Healdsburg, Sonoma County 95448
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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 9 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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    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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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    Amenities & Details
    • 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 22 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 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...
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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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    Healdsburg
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • Private Garden
    • Cable/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, 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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    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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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
    • Cable/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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    Healdsburg
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Secure Parking
    • Cable/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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    Healdsburg
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    • Washer
    • Air Conditioning
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PROPERTY OVERVIEW A lavish retreat for the ultimate group getaway, this stunning 3BR/3BA home with a guest suite is hedged by expansive vineyards and mature trees. Spend an easy afternoon lounging poolside or relaxing in the hot tub. Then enjoy an evening gathered around the fire pit telling...
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    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 3 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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    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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 30 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
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Parking
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PROPERTY OVERVIEW The perfect retreat for a wine country getaway, this lovely 1BR cottage is nestled amongst lush vineyards. Pull up a rocking chair and take in garden views from the patio or spend the day lounging poolside. Go for scenic walks or bike rides through the charming neighborhood,...
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    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Luxury winery estate overlooking the vineyard!1 / 12
    (2)Excellent
    Healdsburg
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Private Garden
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    We greatly enjoyed our stay at the Viszlay House, and cannot wait to return. Our group was 7, though the house can fit up to 12 or more comfortably. The master bedroom is in a...
    Reviewed 1 week ago
    We stayed here as a group of 10 friends from grad school over a weekend in March. They made it very easy to book the place, it was in an excellent location, the house is...
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    About this property
    Plan your perfect Wine Country getaway. Bring your family or close group of friends and stay AT the vineyard! Boasting 5 bedrooms, each with their own bathroom; a gourmet kitchen with wood fired oven and Wolf range. Wrap around deck with stunning views! Come unwind and enjoy your own private slice...
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    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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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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    Location Information
    Healdsburg, Sonoma County 95492
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Healdsburg
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Parking
    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Hot Tub
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PROPERTY OVERVIEW A lavish retreat for a picturesque wine country getaway, this 2BR/2BA is hedged on a lovely 3.5-acre vineyard and mature trees. Take a scenic walk through the charming neighborhood, or explore nearby downtown Healdsburg. Then spend an easy afternoon lounging poolside or relaxing...
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    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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