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Healdsburg Vacation Rentals near Wineries

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    Travelers to Healdsburg are booking April dates now. Secure your vacation rental today, and have the perfect trip.
    30 Matching Rentals in HealdsburgView all 41 rentals
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    Charming Apartment in Dry Creek Valley, Healdsburg1 / 20
    (6)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Newly Renovated home w/ Spa, Gardens, & Spectacular Vineyard Views1 / 21
    (5)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Stunning Wine Country Gated Estate w/ in-ground pool & spa1 / 24
    (22)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Wine Country Get Away in the Heart.1 / 23
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Grill
    • Hot Tub
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 17, 2018
    The accommodation in the vineyards near Healdsburg was fantastic. Great spaces inside and outside for comfort and relaxation. We really enjoyed the outside sitting areas to read...
    Reviewed May 18, 2016
    We especially noted the well equipped kitchen--although we didn't take advantage of it fully on this trip. One could devote energy to activities other than restaurants, and plan...
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    About this property
    This beautiful retreat is in the heart of Russian River Valley. Relax on the patio adjacent to the seasonal creek among the vintage oaks and look out to 55 acres of vineyards and the Russian River. Relax and enjoy the lovely common gardens, with lounge seating, fire pit, outdoor dining area while...
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    Healdsburg, Sonoma County 95448
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Spectacular Two-Story Tuscan Villa Estate Home w/ Spa, Decks & Views1 / 31
    (14)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • DVD Player
    • Grill
    • Hot Tub
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 17, 2018
    The Villa was the perfect place for the trip to the Sonoma wine country with my two daughters and two daughter in laws. We thoroughly enjoyed the charming town of Healdsburg and...
    Reviewed July 7, 2018
    This home is well amenitied. It’s private. The management group is responsive. It’s a lovely home w a great kitchen and beautiful views. All four rooms are sufficient to...
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    About this property
    At the end of a private tree lined country lane, ‘under the Tuscan sun’, vacation in your ‘own private villa’. Nestled among acres of Old Vine Zinfandel, this lovely estate home combines a beautiful setting with the convenience of being just a few minutes away from charming, upscale, and historic...
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    Healdsburg, Sonoma County 95448
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Wine Country Home on Chalk Hill - main house + pool house (up to 12 guests)1 / 29
    (4)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Grill
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    • Washer
    • Hot Tub
    • DVD Player
    • Internet Access
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 30, 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 July 11, 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
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Newly renovated & refurnished one-story 4br/3ba home, sleeps up to 8 guests1 / 25
    (5)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 8, 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 August 9, 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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Studio, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Private Yard
    • Parking
    • DVD Player
    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    • Grill
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    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
    Rental Home - 3 Bathrooms, Sleeps 10
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    Stunning, quiet, contemporary, single-level, eco-friendly home on 2.5 acres1 / 25
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Unheated)
    • Grill
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 16, 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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Upscale, Modern four bedroom, three bath home1 / 20
    (5)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Grill
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 22, 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 September 10, 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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Terra Bella is set in the heart of the beautiful Russian River Valley on Westside road between Thomas George and Porter Creek wineries. This magnificent setting looks out over 55 acres of vineyards bounded by the Russian river. Terra Bella is a 2 1/2 acre property with lovely common gardens to...
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    Healdsburg, Sonoma County 95448
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Housekeeping Included
    • Waterfront
    • Patio
    • Mountain Views
    • Grill
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    • Central Heating
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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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Washer
    • Mountain Views
    • Patio
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    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
    Rental Home - 3 Bedrooms, 5 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to our piece of paradise. This is a brand new contemporary home on a ten-acre parcel located in the Dry Creek Valley appellation. The house is quiet, private, comfortable and spacious. Everything is new. The house is surrounded by vineyards, olive, oak and wildland. Great views. It is a...
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    Healdsburg, Sonoma County 95448
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lovely Healdsburg Vineyard Home - 3br/2ba (up to 8 guests, children welcome)1 / 25
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • DVD Player
    • Hot Tub
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    • Air Conditioning
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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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Beautiful mountain top wine retreat in Healdsburg!1 / 26
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Grill
    • Patio
    • Washer
    • Housekeeping Included
    • Central Heating
    • Mountain Views
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 9, 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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Mountain Views
    • Patio
    • Private Yard
    • 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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Mountain Views
    • Housekeeping Included
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    • DVD Player
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Buena Vista is a Wine Country getaway on the Russian River with Spectacular Views just 5 Minutes 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 an...
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    Healdsburg, Sonoma County 95448
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    • Balcony
    • Air Conditioning
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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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Healdsburg Contemporary Cottage1 / 8
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
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    • Balcony
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    • Terrace
    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 21, 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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Wine Country Cottage1 / 14
    (7)Average
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
    • Air Conditioning
    • Mountain Views
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    • Hot Tub
    • Patio
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 26, 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 June 10, 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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    Healdsburg, Sonoma County 95448
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Hot Tub
    • Patio
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    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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    Healdsburg, Sonoma County 95448
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    • Patio
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    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
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Private Outdoor Pool (Unheated)
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    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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    Healdsburg, Sonoma County 95448
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 7 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • Hot Tub
    • Air Conditioning
    • Balcony
    • Private Yard
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stunning Modern Villa on eight acres, Located in exclusive Shiloh Estates, only minutes to down town Healdsburg and world class Wineries. Extremely private, Triple gated in a natural setting next to famed Mayacama Gold Course. Fully furnished, high end high thread count linens. 4th bedroom is...
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    Healdsburg, Sonoma County 95403
    Rental Home - 4 Bedrooms, 7 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Smoking allowed
    About this property
    div class='rtejustify'>Find your bliss amid the vineyards in Healdsburg Wine Country. This bright, airy, and immaculate home offers everything you want: first-rate entertainment system, super comfortable bedrooms — even a picnic basket and your own bottle of wine from the grapes that surround you!...
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    Healdsburg, Sonoma County 95448
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    • Balcony
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    div class='rtejustify'>Bask in the warmth and beauty of Tuscany — in Sonoma County! Set atop rolling hills among the vineyards, this exquisite estate invites you to transcend beyond everyday routine. You will feel expansive, enjoy a sense of calm, and elevate your perspective. Comfortable...
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    Healdsburg, Sonoma County 95448
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Hot Tub
    • Grill
    • Wi-Fi
    • Terrace
    • Secure Parking
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Residence at Comstock Wines is located on our 17 acre Estate Vineyards and was completed in 2016. The Residence boasts four stunning Master Suites, each offering private entrance, vineyard view terrace, gas fireplace, OrganicPedic beds, 1500 thread count linens, shower with vineyard view window...
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    Healdsburg, Sonoma County 95448
    Rental Home - 4 Bedrooms, 6 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Sauna
    • Washer
    • DVD Player
    • Grill
    • Mountain Views
    • Hot Tub
    • Central Heating
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hello wonderful Guests! We are happy to share our beautiful home that we have built from scratch 8 years ago. We have put much thought and consideration into each aspect of the home. We have children, so we have made this home very family friendly. Children simply love the home and grounds with...
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    Location Information
    Healdsburg, Sonoma County 95448
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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