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Holiday Homes in Middletown

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    All 93 Rentals in Middletown
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    Middletown
    3 Bedrooms, 3 Bathrooms, Sleeps 2 Quick View
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    The following rentals are within 30 kilometres of Middletown.
    Spectacular Two-Story Tuscan Villa Estate Home w/ Spa, Decks & Views1 / 32
    (15)Very good
    Healdsburg, CA
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Wine Country Home On 5 Acres By The Russian  River1 / 16
    (3)Excellent
    Geyserville, CA
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Stunning Wine Country Gated Estate w/ in-ground pool & spa1 / 25
    (22)Excellent
    Healdsburg, CA
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Patio
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Washer
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 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
    VineHaven / Spa, Gardens, & Spectacular Vineyard Views1 / 21
    (5)Excellent
    Healdsburg, CA
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Hot Tub
    • Internet Access
    • Parking
    • Grill
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 January 2019
    We had such a fantastic stay in Healdsburg! We were close to town and close to wineries. The house was beautiful - so neat and clean. The beds were super comfortable, too...
    Reviewed 1 February 2017
    We spent a winter weekend here, and it was a real success. This home is comfortable, spacious and user-friendly. We got a lot of use out of the hot tub, as it was January...
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    About this property
    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 charmer is a lovely, beautifully furnished and decorated, 1600 sq. ft., 3 bedroom/2 bath ranch house with central heat and air conditioning, awaiting your...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Wine Country Home on Chalk Hill - main house + pool house (up to 12 guests)1 / 29
    (4)Very good
    Healdsburg, CA
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Parking
    • Internet Access
    • Washer
    • Grill
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Patio
    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/4.5ba, 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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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    Fulton, CA
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Hot Tub
    • Wi-Fi
    • Central Heating
    • Mountain Views
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Leslie Creek House Treat yourself to an unforgettable wine country getaway at this four-bedroom Santa Rosa home, a stunning Sonoma County escape with a sparkling interior, a fun-filled media room, and picturesque outdoor spaces that include several decks, patios, and a private swimming pool....
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    Fulton, Sonoma County 95404
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Maison du Soleil / Stunning One-Story 4br/3ba home w.Spa, and Ping Pong Table!1 / 25
    (5)Excellent
    Healdsburg, CA
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Air Conditioning
    • Hot Tub
    • Grill
    • Cable/satellite TV
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 October 2018
    The home was exactly as described and seen in pictures. Roomy, clean, stylishly decorated, easily accommodating our group of 7 friends. It was a short 5 minute drive to the town...
    Reviewed 10 August 2016
    This place was very spacious and very clean. The kitchen had all the amenities and appliances we was not expecting to necessarily see (blender, kitchen-aide mixer, salad...
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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...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Healdsburg, CA
    Studio, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Private Garden
    • Parking
    • DVD Player
    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Less than 15 min. to Healdsburg's Plaza Square, also within minutes to jumping off to the Russian River, bicycling, Old Town Windsor, and dozens of wineries! Gorgeous Craftsman home, remodeled, 4BR/3BA two story home with central HVAC, hardwood floors, formal living with TV/DVD, conversational...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bathrooms, Sleeps 10
    Charming Lake View House in a garden setting1 / 35
    (3)Very good
    Kelseyville
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Secure Parking
    • Mountain Views
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 July 2019
    Beautiful house, amazing views. Serene and peaceful location. Fabulous place to rent will definitely stay here again. Charming and cozy with everything you need. Lots of...
    Reviewed 10 April 2018
    Beautiful views, lovely landscapes, extremely private and a very relaxing environment. It has all the amenities you would expect, and everything is in in pristine condition...
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    About this property
    This is a beautiful house over looking magnificent Clear lake and Mt. konocti. It is surrounded by a garden full of roses, lavender, rows of Olive Trees, Cypress Pine trees and a small vinyard. There is plenty to do in this small town. Take your boat on the water and explore the beauty of Clear...
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    Location Information
    Kelseyville, Lake County 95451
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Windsor, CA
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Terrace
    • Children's Pool
    • Washer
    • Balcony
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The biggest Sonoma Coast lodging option is the Three-Bedroom suite, a large furnished family suite with space for up to eight guests that features one king-sized bed in the master bedroom, one queen-sized bed in the guest bedroom, two twin-sized beds in the third bedroom and one queen-sized Murphy...
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    Windsor, Sonoma County 95492
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Clearlake Keys House1 / 8
    (7)Excellent
    Clearlake Oaks
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • DVD Player
    • Air Conditioning
    • Waterfront
    • Washer
    • Cable/satellite TV
    • Mountain Views
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 November 2018
    a wonderful place to getaway with all the comforts of home. It was very quiet and pleasant . The white cranes is the tree across the canal was a pleasant surprise.
    Reviewed 19 August 2018
    Lovely house with great views from the deck. Very clean and comfortable. Owner was very helpful and friendly in all our correspondence.
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    About this property
    Whether you're looking for a romantic weekend of wine-tasting, a relaxing family vacation or a fishing getaway with opportunities right from the dock, Clearlake Keys House is the perfect spot! Situated on a quiet cul-de-sac and channel just minutes from the open waters of beautiful blue Clear Lake,...
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    Clearlake Oaks, Lake County 95423
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
    Recently Remodeled1 Bedroom Apartment near Downto1 / 9
    (1)Excellent
    St. Helena, CA
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Outdoor Dining Area
    • Washer
    • Patio
    • Parking
    • Air Conditioning
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 January 2018
    I had the pleasure of staying in this unit for over 2 months in late 2015 to early 2016 while consulting in the area. It was booked by the company and I was thrilled with the...
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    About this property
    Elegantly furnished 1 bedroom, 1 bath apartment 3 blocks from Main Street St. Helena. Air conditioned, king bed, large dresser with drawers, walk-in closet, gourmet kitchen, 2 HDTVs, DVD, cable service, desk, sofa bed, and laundry closet with washer and dryer. Private patio with table, chairs and...
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    St. Helena, Napa Valley 94574
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Geyserville, CA
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Hot Tub
    • Washer
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Getaway on Dry Creek Experience the best of California wine country at this two-bedroom Healdsburg home, where you'll enjoy a private outdoor hot tub, two patios and a deck, and an ideal location close to restaurants and tasting rooms. This dog-friendly retreat sits on a tree-lined property...
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    Geyserville, Sonoma County 95448
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Windsor, CA
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Washer
    • Private Garden
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Armida Vineyards Cottage 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...
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    Windsor, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    West Dry Creek View1 / 37
    (4)Very good
    Healdsburg, CA
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Hot Tub
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 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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    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...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Healdsburg, CA
    3 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Washer
    • Mountain Views
    • Patio
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    WHISPERING OAKS ESTATE This Elegant Villa offers World Class Views, High End Appointments, a Chef Inspired Kitchen, Indoor and OutdoorDining and Entertainment Areas, including an Outdoor Firepit to enjoy the evening with family and friends. The property is private yet only 10 minutes to town,...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 5 Bathrooms, Sleeps 8
    Clearlake
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Grill
    • Washer
    • Wi-Fi
    • Mountain Views
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    FALCON HAVEN Come enjoy all that Clearlake has to offer at Falcon Haven. World class Freshwater Fishing, Water Skiing, Site Seeing, or just relaxing on the private waterfront patio and decks. Falcon Haven has 2 stories all with spectacular lake views and Mt Konocti. The main level features an...
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    Clearlake, Lake County 95422
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 8
    Windsor, CA
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Terrace
    • Washer
    • Balcony
    • Children's Pool
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect for families and small groups traveling together, this option is equipped with one king-sized bed in the master bedroom, two twin beds in the guest bedroom and one queen-sized Murphy bed in the living room. With space for up to six people, this comfortable family suite features a separate...
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    Windsor, Sonoma County 95492
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Healdsburg, CA
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Washer
    • Central Heating
    • Wi-Fi
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casa Pavone Nestled in the Alexander Valley mid-way between Healdsburg and Calistoga on picturesque Chalk Hill Road is Casa Pavone, a traditional farmhouse situated along the Maacama Creek. In a little valley of its own, this nearly three-acre property is entirely secluded. Ideal for adults and...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Healdsburg, CA
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Dry Creek Retreat Discover the luxuries of wine country living at Dry Creek Retreat, an exquisite 55-acre vineyard, 5,000-case state-of-the-art winery, and luxury home in the rolling hills of Healdsburg. Not only does this vineyard make world-class wines, but it also offers access to a gorgeous...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Windsor, CA
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Children's Pool
    • Terrace
    • Hot Tub
    • Washer
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Each condo is outfitted with one king-sized bed in the master bedroom, plus queen-sized Murphy bed in the separate living area. Ideal for two to four guests, this comfortable rental features a fully equipped kitchen, private terrace or patio and gas fireplace. You'll also have high-speed Internet...
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    Windsor, Sonoma County 95492
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Upscale, Modern four bedroom, three bath home1 / 20
    (5)Very good
    Healdsburg, CA
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • 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
    Fulton, CA
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Washer
    • Mountain Views
    • Balcony
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    WineCamp The WineCamp concept is rooted in the rural ambiance of working local vineyards and craft breweries. This wine and beer-themed property is not suitable for children. Adults, it’s your turn to luxuriate in sleek modern architecture right in the heart of California's original wine country...
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    Fulton, Sonoma County 95401
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Limerick Lane / Stunning, Quiet, Contemporary, Single-Level, Eco-Friendly1 / 25
    (3)Excellent
    Healdsburg, CA
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Grill
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Patio
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 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
    Healdsburg, CA
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • 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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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Healdsburg, CA
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
    • Washer
    • Grill
    • Wi-Fi
    • Mountain Views
    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    RIVER VIEW LODGE River View Lodge appeals to guests with its spectacular riverfront setting, spacious river view deck, charming décor, exceptionally comfortable beds and linens, outstanding cleanliness, and quality amenities. River View features private river access, and includes kayaks, paddles...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Modern Lux Wine Country Ranch1 / 37
    (1)Excellent
    Calistoga, CA
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Mountain Views
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Patio
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 November 2018
    My family’s stay at the Mayastoga Wine Country Ranch exceeded our expectations! The house and property blew us away and look even better in person than in the photos. The host...
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    About this property
    Modern luxury meets Napa Valley Wine Country ranch style in this beautifully 17 acre property nestled in a private valley in the Mayacamas Mountains 1,200 feet above Calistoga. We call it 'Mayastoga.' Learn more about 'Mayastoga' and 'Mayastoga Ranches' by searching the web. This beautiful home...
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    Location Information
    Calistoga, Napa Valley 94515
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
    Clearlake
    5 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Washer
    • Grill
    • Air Conditioning
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    CHATEAU CLEAR LAKE Chateau Clear Lake will be unavailable most of 2018 as we house a family who lost their home during the fire, please contact us for available dates. Come enjoy all that Clearlake has to off at Chateau Clearlake. World class Freshwater Fishing, Water Skiing, Site Seeing, or just...
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    Location Information
    Clearlake, Lake County 95422
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 16
    Beautiful mountain top wine retreat in Healdsburg!1 / 26
    (1)Excellent
    Healdsburg, CA
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Central Heating
    • Mountain Views
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 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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    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 Healdsburg...
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    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Big Oak Vineyard / Vineyard Views, 3br/2ba, w.Spa and Attached to a Winery!1 / 25
    (4)Excellent
    Healdsburg, CA
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Shaded by a 100-year-old oak tree, this very special home ‘lives’ on 30 vineyard acres and is off Dry Creek Road, just one mile west of the north end of charming, upscale, historic, Healdsburg in the heart of Sonoma County’s Wine Country. Newly renovated, this 3 bedroom/2 bath, Ranch House with...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Best place on the Lake1 / 7
    (1)Very good
    Kelseyville
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • Air Conditioning
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    • Waterfront
    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 November 2016
    Loved the lake front accessibility of this rental. The kitchen was great for cooking and the kitchen table over looked the gorgeous lake! We would definitely stay here again.
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    About this property
    If you are looking for the perfect lake house, here it is! Great dock, fishing, boat ramp. Well equipped kitchen, lovely furnishings, comfy beds. It is a truly wonderful house. There's even a PacMan machine. Long term stays are recommended. Lots to do if you like to look at birds or go hiking,...
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    Kelseyville, Lake County 95451
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Windsor, CA Cottage in Sonoma's Wine Country1 / 21
    (6)Excellent
    Windsor, CA
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Garden
    • Grill
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    • Outdoor Dining Area
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 March 2016
    A fantastic 2 bedroom guest house. Warm, comfy, incredibly well appointed. You will want for nothing. If you are in the area, this is the place you want to stay.
    Reviewed 19 October 2015
    Justine provides a well-appointed and stylish accommodation in the heart of the wine country. The cottage is immaculate and everything one might need to prepare meals at-home...
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    About this property
    The Carriage House is a 800 sq/ft single level cottage in a unique country property setting, within walking distance to our sleepy Town Green where there is a seasonal farmer's market, music and movie nights. Our home sits on a level private acre and boasts mature trees for shade, open sunny areas...
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    Windsor, Sonoma County 95492
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Healdsburg, CA
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    REDWOOD RIVER HOUSE Cozy Riverfront Home with Peace and Seclusion awaits you in the heart of Healdsburg. Tucked into one of the best locations on Healdsburg's Riverfront awaits this upscale cottage. Open Floor Plan with lots of Natural Light and Large Expansive Deck. Redwood River House is a...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Healdsburg, CA
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • Private Garden
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    • Private Outdoor Pool (Heated)
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    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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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
    St. Helena, CA
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Porch
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Very quiet and private, yet only a 15 minute walk downtown to Main Street where you'll find The Culinary Institute of America, Giugni's Delicatessen, Model Bakery, Gott's Roadside and Dean & Deluca. Also local are world-class restaurants such as PRESS, Market, Farmstead, Tra Vigne, Cindy's...
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    St. Helena, Napa Valley 94574
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Healdsburg, CA
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Drive down a tree-lined road. Vineyard is on left, beautiful gardens and bocce court in front, and garden area to the right in which to sit or stroll. Walk into a dramatic entry, and you'll see formal living room and dining rooms on the right, with a half bath across the hallway. To your left,...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Healdsburg, CA
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Healdsburg, CA
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
    About this property
    Visit our stunning new home for an ultimate wine country experience. It is your base camp for your wine tasting journey. Walk to world class wineries or ride your bike along the rows of vines. Waltz through our vineyard and picnic under an olive tree - while taking in the amazing views. The home...
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    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Healdsburg, CA
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Alexander Valley Retreat / Private, Country, Views and only 3 miles to town!1 / 23
    (1)Excellent
    Healdsburg, CA
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is located in northeast Healdsburg on Alexander Valley Road, at the mouth of the Alexander Valley and just minutes from the Dry Creek Valley. This beautiful, 2-story 2,400 sqft home is well-maintained, with mature English garden style landscaping, flagstone walkways and back patio, fruit...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Healdsburg Contemporary Cottage1 / 8
    (2)Excellent
    Healdsburg, CA
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
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    • Terrace
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    As we travel for 6 months of the year we are experts at holiday rentals and know that gaining access to the property is usually the most difficult thing to accomplish. In this...
    Reviewed 22 August 2017
    This was the best money I have ever spent on a vacation property. Where do I start? This quaint, tastefully decorated cottage is perfectly located. It is close enough to the...
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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...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Healdsburg, CA
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    HEALDSBURG VILLA This sprawling estate home offers easy access to every wine country amenity imaginable. Watch hot air balloons take off from the rear veranda while surrounded by acres of vines. Minutes to river fun and a walk to world class wineries. Relaxing seclusion to intense action at the...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
    Geyserville, CA
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Mountain Views
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Lake Sonoma Ranch Estates in Dry Creek Valley. Experience unparalleled views and amazingly comfortable luxury king-sized beds with individual TVs each of the three bedrooms. If you like to cook, the huge kitchen features vaulted ceilings, double ovens, gas range, microwave, dishwasher,...
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    Geyserville, Sonoma County 95441
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Healdsburg, CA
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
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    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
    Geyserville, CA
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Cable/satellite TV
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    • Private Outdoor Pool (Unheated)
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning vineyard estate home is perched on a hill with spectacular 360-degree vineyard views of Geyser Peak, Alexander Valley and the Dry Creek hills. This spacious home features a lovely pool & spa, gourmet kitchen, wrap-around veranda, vaulted ceilings with crown moldings, hardwood...
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    Geyserville, Sonoma County 95404
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Healdsburg, CA
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    • Mountain Views
    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Buena Vista is a Wine Country getaway on the Russian River with Spectacular Views just a short drive from Healdsburg Plaza. When you reserve this 2400 square foot, 3 bedroom, 3 bath home, beautiful, panoramic views are just one of the many amenities you will be able to enjoy. The Buena Vista is...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Wine Country Townhouse1 / 11
    (3)Average
    Windsor, CA
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
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    Reviewed 24 July 2018
    My family of five and I have had the pleasure of renting this Townhouse five different summers. We head to Nor Cal every summer and this place has it all. The home is spotless...
    Reviewed 8 February 2018
    We left hot Florida and had a great time in California wine country. Instead of a usual hotel we joined our friends at this townhouse. After long days of sight seeing we came...
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    About this property
    Upstairs downtown condominium on the Windsor Green, walk to coffee, restaurants, shopping. Concerts in summer. Main floor has beautifully decorated living room with fireplace, Flat screen TV, DVD, sofa, chairs, dining area and kitchen and half bath. Deck looks over to historic railroad station and...
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    Windsor, Sonoma County 95492
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Healdsburg, CA
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Private Outdoor Pool (Unheated)
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    • 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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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Wine Country Cottage1 / 14
    (7)Average
    Healdsburg, CA
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
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    • Mountain Views
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 11 June 2013
    Yes, this cottage is comfortable and well furnished. Full kitchen, great hot tub, comfortable beds, lovely setting in a real vineyard. BUT: it is located off a fairly busy road...
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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...
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    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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