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Vacation Rentals nearby Chalk Hill Winery

10300 Chalk Hill Rd, Healdsburg, California 95448-9558
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    Travellers to Healdsburg are booking November dates now. Secure your vacation rental today, and have the perfect trip.
    All 86 Rentals in Healdsburg
    Wine Country Home on Chalk Hill - main house + pool house (up to 12 guests)1 / 29
    (4)Very good
    4.4 kilometres from Chalk Hill Winery
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Limerick Lane / Stunning, Quiet, Contemporary, Single-Level, Eco-Friendly1 / 25
    (3)Excellent
    5.8 kilometres from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    7.9 kilometres from Chalk Hill Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    7.7 kilometres from Chalk Hill Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Welcome to heavenly Healdsburg and Hilltop's Vista Villa! This gated 2-bedroom, 2-bath luxury Tuscan inspired villa is located only 3 miles from the historic Healdsburg plaza on one hillside acre near the top of the east side of Fitch mountain and is the only home this close to the top! This...
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    9.5 kilometres from Chalk Hill Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    12.9 kilometres from Chalk Hill Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    5.9 kilometres from Chalk Hill Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Unheated)
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    About this property
    Xanadu Healdsburg Luxury Vacation home in Healdsburg. In the Heart of Sonoma County Wine Country, Healdsburg is the hub of the Dry Creek, Alexander Valley and Russian River Wine Regions. The home is just Five minutes from the Healdsburg Plaza Square with dozens of Winery Tasting Rooms, Award...
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    5.9 kilometres from Chalk Hill Winery
    4 Bedrooms, 7 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
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    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
    Holiday Rental House - 4 Bedrooms, 7 Bathrooms, Sleeps 8
    Beautiful Views!  Dry Creek Valley Retreat with Deck & Pool, 5 min to Healdsburg1 / 46
    (47)Excellent
    13.3 kilometres from Chalk Hill Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Crossroads Vineyard:  In the Heart of Healdsburg Wine Country1 / 23
    (88)Excellent
    12.3 kilometres from Chalk Hill Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Breathtaking Dry Creek Estate - Modern, Spacious, Luxury!1 / 33
    (5)Excellent
    14.5 kilometres from Chalk Hill Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    12.9 kilometres from Chalk Hill Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Spectacular view of Dry Creek Valley1 / 26
    (1)Excellent
    11.3 kilometres from Chalk Hill Winery
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Pet Friendly Wine Country Getaway On The Russian River Just 5 Minutes From Town1 / 44
    (57)Very good
    7.8 kilometres from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Enchanting Wine Country Villa1 / 24
    (3)Excellent
    6.1 kilometres from Chalk Hill Winery
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    Luxury Vineyard Estate House and Guest House1 / 45
    (73)Excellent
    5.9 kilometres from Chalk Hill Winery
    5 Bedrooms, 4 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 4
    Bunkhouse at Side Road Farm charming one bedroom cottage1 / 35
    (16)Excellent
    9.2 kilometres from Chalk Hill Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Safe Retreat: Bicyclists, Birders, Wine Lovers, River Revelers Welcome!1 / 14
    (66)Excellent
    11.8 kilometres from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    11.1 kilometres from Chalk Hill Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Beautiful Studio Getaway  in the Heart of Wine Country1 / 12
    (36)Excellent
    11.6 kilometres from Chalk Hill Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Vineyard Guest House1 / 31
    (17)Excellent
    19.5 kilometres from Chalk Hill Winery
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    4,700 ft 4 bed & 4 bath ranch, Summer 2020, fully catered plant based retreats1 / 47
    (16)Excellent
    14.3 kilometres from Chalk Hill Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    9.6 kilometres from Chalk Hill Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Enjoy the Sunset from Upscale Home Among Vineyards — short walk to Healdsburg1 / 48
    (53)Excellent
    10.4 kilometres from Chalk Hill Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Stunning Mountain Top Estate with View Over Dry Creek Vineyards1 / 28
    (18)Excellent
    20.6 kilometres from Chalk Hill Winery
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    Dry Creek Cottage - Healdsburg1 / 6
    (48)Excellent
    11.5 kilometres from Chalk Hill Winery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Private Wine Country Retreat-Luxury estate, pool, hot tub, 3 miles to town1 / 42
    (38)Excellent
    13.5 kilometres from Chalk Hill Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    The Cabin on Fitch Mountain1 / 37
    (6)Very good
    7.6 kilometres from Chalk Hill Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Tanda Tula, Wine Country Sanctuary1 / 28
    (74)Excellent
    18.9 kilometres from Chalk Hill Winery
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Creek Front Vineyard, West Dry Creek Healdsburg CA1 / 30
    (9)Excellent
    18.8 kilometres from Chalk Hill Winery
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
    Wine country getaway; stay in a winery1 / 12
    (10)Excellent
    15.3 kilometres from Chalk Hill Winery
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Updated cabin, right on Russian River, amazing views & location!1 / 23
    (14)Excellent
    7.4 kilometres from Chalk Hill Winery
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Downtown Healdsburg Loft - (30 day minimum rentals only)1 / 19
    (1)Excellent
    10.0 kilometres from Chalk Hill Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Healdsburg, Sonoma County
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Mountain Cottage near Russian River, hiking and downtown, family and pet friendl1 / 27
    (5)Very good
    8.8 kilometres from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Luxury Wine Country Home in the Heart of Healdsburg with a Private Pool.1 / 49
    (11)Excellent
    15.6 kilometres from Chalk Hill Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Healdsburg River Front Oasis Retreat.1 / 28
    (48)Excellent
    7.8 kilometres from Chalk Hill Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Morning Dew- A Riverfront Healdsburg Home1 / 27
    (12)Excellent
    7.8 kilometres from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
    Newly Listed 4BR/4.5BA Gorgeous 17 Acre Estate/Pool/Hot Tub/5 mins - Hburg Plaza1 / 23
    (15)Excellent
    11.9 kilometres from Chalk Hill Winery
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    6.1 kilometres from Chalk Hill Winery
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    The perfect location for your Healdsburg getaway. Three separate buildings including a three bedroom house, a bright and airy studio shed with an outdoor shower, and your own wine tasting bar in our family barn. Modern design in a rustic setting right across the road from J Winery and Rodney Strong...
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
    New Listing! Private home w/ beautiful garden, private hot tub, & great location1 / 25
    (2)Excellent
    6.6 kilometres from Chalk Hill Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Hilltop Hideaway:  Bright, Fresh, Modern, Views And Only 2 Miles To Plaza1 / 49
    (100)Excellent
    7.5 kilometres from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Beautiful Mountain Top retreat less than 10 mins from downtown Healdsburg!1 / 35
    (79)Excellent
    8.1 kilometres from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Wine Country Home on Chalk Hill - main house + pool house (up to 12 guests)1 / 29
    (25)Very good
    4.4 kilometres from Chalk Hill Winery
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Central Heating
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    Healdsburg, Sonoma County
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    Healdsburg Cottage in Historic Downtown - Walk to the Plaza1 / 25
    (111)Excellent
    9.8 kilometres from Chalk Hill Winery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Cabin In An Old Vine Zinfandel Vineyard. Dry Creek Valley. Five Miles To Plaza.1 / 11
    (150)Excellent
    14.4 kilometres from Chalk Hill Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Secluded Valley Retreat1 / 20
    (58)Excellent
    18.9 kilometres from Chalk Hill Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
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    • Private Outdoor Pool (Unheated)
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    15.4 kilometres from Chalk Hill Winery
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
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    Pet friendly
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    Smoking allowed
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    Fitch Mountain Lookout: View, Hot Tub, Fireplace, Beach Access1 / 16
    (72)Very good
    7.5 kilometres from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Modern country cottage: swimming pool, privacy, vineyard & 5 min. to Healdsburg1 / 36
    (137)Very good
    6.1 kilometres from Chalk Hill Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    Pet friendly
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Healdsburg - Chalk Hill Wine Country Cottage1 / 24
    (157)Excellent
    1.1 kilometres from Chalk Hill Winery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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