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Healdsburg House Rentals

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    Travellers to Healdsburg are booking April dates now. Secure your vacation rental today, and have the perfect trip.
    34 Matching Rentals in HealdsburgView all 44 rentals
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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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    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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    Newly Renovated home w/ Spa, Gardens, & Spectacular Vineyard Views1 / 21
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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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
    • Air Conditioning
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    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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Grill
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    • Balcony
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    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
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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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    • Internet Access
    • Private Outdoor Pool (Unheated)
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    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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)
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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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Parking
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ideally located on 7 hillside acres, in the famed Dry Creek Valley, this absolutely stunning, new, modern Wine Country home is a spectacular retreat nestled in Mother Nature’s paradise, with forever easterly views of the Dry Creek Valley. This magnificent architectural marvel was designed by John...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    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
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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
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    West Dry Creek View1 / 37
    (4)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 15, 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
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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 Garden
    • Wi-Fi
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cottage provides the true Dry Creek Valley wine country experience. with 270 degree views - from Mt. St. Helena in the east to the Pacific Coast Range in the west. Swim in the solar heated lap pool and then relax by the pool while soaking up the view. Walk through the vineyards and the rose...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Central Heating
    • Mountain Views
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    • Waterfront
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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
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Waterfront
    • Washer
    • Mountain Views
    • Grill
    • Hot Tub
    • Central Heating
    • Wi-Fi
    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
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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
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    • 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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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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
    • Cable/satellite TV
    • Hot Tub
    • Patio
    • Grill
    Suitability
    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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Mountain Views
    • Housekeeping Included
    • Air Conditioning
    • DVD Player
    • Grill
    • 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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Internet Access
    • Secure Parking
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Balcony
    • Air Conditioning
    Suitability
    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
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    Private estate in Alexander Valley/ Views! 3 miles to town1 / 23
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
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    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
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 two miles north of central...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Terrace
    • Hot Tub
    • Balcony
    • Central Heating
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    • DVD Player
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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
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Secure Parking
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    • Private Outdoor Pool (Heated)
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    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
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    Studio, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
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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
    Holiday Rental House - 3 Bathrooms, Sleeps 10
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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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    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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 country, this bright and...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • Parking
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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
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
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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
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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, the nearly three-acre property is entirely secluded. Ideal for adults and children alike,...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
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    • Air Conditioning
    • Internet Access
    • DVD Player
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    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
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    4 Bedrooms, 7 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • Hot Tub
    • Air Conditioning
    • Balcony
    • Private Garden
    • Terrace
    Suitability
    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
    Holiday Rental House - 4 Bedrooms, 7 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
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    • Patio
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    • 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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    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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    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Patio
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is the best destination in Healdsburg for extended families attending weddings, on summer or spring vacations, or for groups of adults on holiday to cycle or taste wines. Designed as a family compound on a gated estate by the shore of the Russian River, it offers unmatched privacy along with a...
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    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    3 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Wi-Fi
    • Central Heating
    • Balcony
    • Mountain Views
    • Grill
    • DVD Player
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2nd floor: 11 foot ceilings. Beautiful, gourmet kitchen with stunning views. Kitchen is equipped with a Thermador 6 burner (and grill) gas stove top and double electric oven. Butcher block counter tops. Dishwasher, Professional quality knives and cookware. Large microwave. Spacious walk-in pantry....
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    Location Information
    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 6 Bathrooms, Sleeps 8
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