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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 September dates now. Secure your vacation rental today, and have the perfect trip.
    All 141 Rentals in Healdsburg
    Stunning NEW Modern Farmhouse, Just 3 Blocks from Healdsburg Plaza1 / 28
    (5)Excellent
    9.5 kilometres from Chalk Hill Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    12.9 kilometres from Chalk Hill Winery
    5 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Beautiful Views!  Dry Creek Valley Retreat with Deck & Pool, 5 min to Healdsburg1 / 46
    (66)Excellent
    13.3 kilometres from Chalk Hill Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    6.2 kilometres from Chalk Hill Winery
    3 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 5 Bathrooms, Sleeps 10
    Enjoy a Slice Of Country--Two miles to Downtown Healdsburg1 / 35
    (40)Excellent
    12.3 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
    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
    Superb Healdsburg Location, Spectacular Views, Minutes to Town1 / 48
    (39)Excellent
    8.8 kilometres from Chalk Hill Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
    Pet Friendly Wine Country Getaway On The Russian River Just 5 Minutes From Town1 / 39
    (65)Very good
    7.8 kilometres from Chalk Hill Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Secluded Luxury Vineyard Estate Guest House1 / 17
    (85)Excellent
    5.9 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
    Bunkhouse at Side Road Farm charming one bedroom cottage1 / 34
    (30)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
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    NewTree Ranch Estate Retreat, Eco-Luxury Farm Stay 4.7 miles to Healdsburg1 / 51
    (22)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
    Dry Creek Cottage - Healdsburg1 / 9
    (89)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
    Creek Front Vineyard, West Dry Creek Healdsburg CA1 / 30
    (27)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
    Private 3 Bed + Cottage Wine Country Estate With Pool And More1 / 23
    (34)Excellent
    11.7 kilometres from Chalk Hill Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Sauna
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Wine country getaway; stay in a winery1 / 12
    (17)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
    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
    (4)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
    Luxury Wine Country Home in the Heart of Healdsburg with a Private Pool.1 / 50
    (31)Excellent
    15.5 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
    A redwood retreat in the heart of Sonoma County wine country (w/ Fiber Internet)1 / 50
    (16)Very good
    12.2 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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    Spectacular view of Dry Creek Valley1 / 24
    (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
    Dry Creek Valley Home and Vineyard1 / 24
    (40)Excellent
    15.4 kilometres from Chalk Hill Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Entire Resort Villa *pool-spa-tennis-wine-dine*1 / 36
    (8)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
    Safe Retreat: Bicyclists, Birders, Wine Lovers, River Revelers Welcome!1 / 14
    (82)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
    Beautiful Studio Getaway  in the Heart of Wine Country1 / 12
    (66)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
    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
    luxuriously appointed new large guest suite in a landmark Victorian1 / 21
    (50)Excellent
    11.7 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
    The Cabin on Fitch Mountain1 / 37
    (37)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 / 30
    (107)Excellent
    18.9 kilometres from Chalk Hill Winery
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    Mountain Cottage near Russian River, hiking and downtown, family and pet friendl1 / 27
    (27)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
    Healdsburg Bliss House-Sonoma Wine Country Sweeping Panoramic Vineyard Views1 / 14
    (150)Excellent
    10.9 kilometres from Chalk Hill Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Healdsburg River Front Oasis Retreat.1 / 28
    (98)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 / 35
    (24)Very good
    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
    11.9 kilometres from Chalk Hill Winery
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
    6.0 kilometres from Chalk Hill Winery
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    20.8 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
    9.4 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
    7.6 kilometres from Chalk Hill Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Beautiful Mountain Top retreat less than 10 mins from downtown Healdsburg!1 / 39
    (91)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
    Santini Farmhouse--Luxury Cottage in the Center of Dry Creek Valley1 / 45
    (13)Excellent
    21.0 kilometres from Chalk Hill Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    9.2 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
    Dog Friendly Healdsburg Vineyard Estate Cottage with Lap Pool/Incredible Views1 / 18
    (46)Excellent
    20.3 kilometres from Chalk Hill Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Outdoor Pool (Unheated)
    • Balcony
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Private Vineyard Haven1 / 44
    (10)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
    Views, Hot Tub, Fireplace, Semi-Private Beach Close By , Pet-Friendly1 / 16
    (117)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
    19.5 kilometres from Chalk Hill Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Modern country cottage: swimming pool, privacy, vineyard & 5 min. to Healdsburg1 / 47
    (162)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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    • DVD Player
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    15.8 kilometres from Chalk Hill Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    7.7 kilometres from Chalk Hill Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Luxe Penthouse on the River1 / 44
    (8)Excellent
    7.9 kilometres from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    6.3 kilometres from Chalk Hill Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    • Internet Access
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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