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Vacation Rentals near Chalk Hill Winery

10300 Chalk Hill Rd, Healdsburg, California 95448-9558
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    Travelers to Healdsburg are booking October dates now. Secure your vacation rental today, and have the perfect trip.
    All 24 Rentals in Healdsburg
    Stunning Wine Country Gated Estate w/ in-ground pool & spa1 / 24
    (22)Excellent
    4.1 miles from Chalk Hill Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Stunning, quiet, contemporary, single-level, eco-friendly home on 2.5 acres1 / 25
    (3)Excellent
    3.9 miles from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 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
    3.0 miles from Chalk Hill Winery
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Newly renovated 2-story custom Estate - 5br+/3.5ba home, sleeps 101 / 25
    (2)Excellent
    3.9 miles from Chalk Hill Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Washer
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Hot Tub
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Very well located about 3.5 miles southeast of Healdsburg’s famed Plaza, the lovely Eastside Estate sits on 2+ beautifully manicured and wooded acres among the vineyards of the Russian River Valley appellation. Newly renovated, and professionally decorated and furnished, this Estate is nothing...
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    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Upscale, Modern four bedroom, three bath home1 / 20
    (5)Very good
    3.8 miles from Chalk Hill Winery
    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 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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4.5 miles from Chalk Hill Winery
    Studio, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Private Yard
    • 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
    Rental Home - 3 Bathrooms, Sleeps 10
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    4.5 miles from Chalk Hill Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Terrace
    • Hot Tub
    • Balcony
    • Central Heating
    • Grill
    • Washer
    • DVD Player
    Suitability
    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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4.1 miles from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Washer
    • Parking
    • Grill
    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    Suitability
    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3.3 miles from Chalk Hill Winery
    4 Bedrooms, 7 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • Hot Tub
    • Air Conditioning
    • Balcony
    • Private Yard
    • 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
    Rental Home - 4 Bedrooms, 7 Bathrooms, Sleeps 8
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    4.0 miles from Chalk Hill Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Patio
    • Washer
    • Parking
    • Hot Tub
    • Internet Access
    • Grill
    Suitability
    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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    Location Information
    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Windsor, CA Cottage in Sonoma's Wine Country1 / 21
    (6)Excellent
    3.4 miles from Chalk Hill Winery
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Yard
    • Grill
    • Washer
    • Central Heating
    • Parking
    • Outdoor Dining Area
    • Internet Access
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 7, 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 October 18, 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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3.3 miles from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • 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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3.3 miles from Chalk Hill Winery
    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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3.3 miles from Chalk Hill Winery
    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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Wine Country Townhouse1 / 11
    (3)Average
    2.9 miles from Chalk Hill Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 23, 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 February 7, 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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3.3 miles from Chalk Hill Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Grill
    • Central Heating
    • Wi-Fi
    • Washer
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The WorldMark Windsor resort is located on ten acres with multiple 3-story buildings, all with elevators. Nestled into the Russian River Valley in Sonoma County, Windsor is a small town with deep roots in farming and, more recently, winemaking. You'll enjoy the area's family-owned wineries and the...
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    Windsor, Sonoma County
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.5 miles from Chalk Hill Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Washer
    • Internet Access
    • Hot Tub
    • Cable/satellite TV
    • DVD Player
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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. This two-level...
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    Santa Rosa, Sonoma County
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3.3 miles from Chalk Hill Winery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Grill
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Greetings from Windsor, California, located in the heart of Sonoma County's Russian River Valley. Whether you're here for the wine, fine dining, golf, scenery or to relax, you're sure to fal in love with the beautiful WorldMark Windsor resort. WorldMark Windsor is located on 10 acres with multiple...
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    Location Information
    Windsor, Sonoma County
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2.5 miles from Chalk Hill Winery
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Patio
    • Washer
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    DAYS OF WINE AND ROSES - WINE COUNTRY ESCAPE PERFECT HARVEST FAIR LOCATION!!! Looking for a peaceful retreat, but one that’s close to everything? Then come and relax at the welcoming, spacious, open, newly-remodeled Rose Cottage. Full of inviting ambiance and modern luxury, the home is in a great...
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    Location Information
    Windsor, Sonoma County
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2.9 miles from Chalk Hill Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • DVD Player
    • Air Conditioning
    • Grill
    • Terrace
    • Parking
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Upstairs Windsor Town Green condominium with high end furnishings, fireplace, a/c, fireplace, full kitchen, dining and sleeping for six guests. Everything convenient located within just a few steps out the front door including coffee, restaurants, pub, and summer concerts. Walk into the condo...
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    Windsor, Sonoma County
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1.8 miles from Chalk Hill Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Washer
    • Terrace
    • Central Heating
    • Hot Tub
    • Balcony
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This newly remodeled 3 bedroom home is the perfect wine country getaway with breathtaking vineyard views! The main level has an open floor plan with the living room, dining room, kitchen and half bathroom on one level. There is a deck off the kitchen with an outdoor BBQ, patio table and 5-8 person...
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    Windsor, Sonoma County
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    3.3 miles from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
    • Air Conditioning
    • Patio
    • DVD Player
    • Washer
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The WorldMark Windsor resort is located on ten acres with multiple 3-story buildings, all with elevators. Nestled into the Russian River Valley in Sonoma County, Windsor is a small town with deep roots in farming and, more recently, winemaking. You'll enjoy the area's family-owned wineries and the...
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    Location Information
    Windsor, Sonoma County
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3.4 miles from Chalk Hill Winery
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Air Conditioning
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Washer
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Got some wine lovers to impress? Book a vacation in this spacious country home in Santa Rosa, with spectacular views, top of the line decor, hot tub, and a gourmet kitchen. It’s 5BR, 3.5BA and sleeps 12, so there’s plenty of room for a crowd! INSIDE THE RENTAL As you enter this elegant home, it’s...
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    Santa Rosa, Sonoma County
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 8
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    3.3 miles from Chalk Hill Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Patio
    • Hot Tub
    • Terrace
    • DVD Player
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The WorldMark Windsor resort is located on ten acres with multiple three-story buildings, all with elevators. Nestled into the Russian River Valley in Sonoma County, Windsor is a small town with deep roots in farming and, more recently, winemaking. You'll enjoy the area's family-owned wineries and...
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    Location Information
    Windsor, Sonoma County
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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