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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 July dates now. Secure your vacation rental today, and have the perfect trip.
    All 183 Rentals in Healdsburg
    Stunning NEW Modern Farmhouse, Just 3 Blocks from Healdsburg Plaza1 / 27
    (6)Excellent
    5.9 miles from Chalk Hill Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Remodeled, Spotless & Only 3 Blocks from the Plaza!1 / 18
    6.3 miles from Chalk Hill Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Ultimate Romance on Dry Creek 5 mins From Town!1 / 30
    7.6 miles from Chalk Hill Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    The Ultimate Wine Lover's Experience1 / 13
    3.8 miles from Chalk Hill Winery
    3 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 5 Bathrooms, Sleeps 10
    Enjoy a Slice Of Country--Two miles to Downtown Healdsburg1 / 30
    (41)Excellent
    7.6 miles from Chalk Hill Winery
    2 Bedrooms, 1 Bathroom, Sleeps 2 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 2
    Breathtaking Dry Creek Estate - Modern, Spacious, Luxury!1 / 30
    (5)Excellent
    9.1 miles from Chalk Hill Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Superb Healdsburg Location, Spectacular Views, Minutes to Town1 / 30
    (40)Excellent
    5.4 miles from Chalk Hill Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 7
    Pet Friendly Wine Country Getaway On The Russian River Just 5 Minutes From Town1 / 30
    (65)Very good
    4.8 miles from Chalk Hill Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Bunkhouse at Side Road Farm charming one bedroom cottage1 / 30
    (31)Excellent
    5.7 miles from Chalk Hill Winery
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    • Skiing: Property Is In A Ski Resort
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    Healdsburg, Sonoma County
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 1
    Secluded Luxury Vineyard Estate Guest House1 / 17
    (85)Excellent
    3.6 miles from Chalk Hill Winery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    120-acres of peace and tranquility, 10 minutes from downtown Healdsburg1 / 30
    (22)Excellent
    8.8 miles from Chalk Hill Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Healdsburg Downtown Condo1 / 18
    6.0 miles from Chalk Hill Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Spectacular View Estate 5min Away1 / 30
    (17)Excellent
    8.8 miles from Chalk Hill Winery
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 12
    Dry Creek Cottage - Healdsburg1 / 7
    (97)Excellent
    7.1 miles from Chalk Hill Winery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Creek Front Vineyard, West Dry Creek Healdsburg CA1 / 30
    (31)Excellent
    11.5 miles from Chalk Hill Winery
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 6 Bedrooms, 7 Bathrooms, Sleeps 12
    Private 3 Bed + Cottage Wine Country Estate With Pool And More1 / 23
    (34)Excellent
    7.2 miles from Chalk Hill Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Updated cabin, right on Russian River, amazing river access & location!1 / 24
    (38)Excellent
    4.4 miles from Chalk Hill Winery
    2 Bedrooms, 3 Bathrooms, Sleeps 2 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 2
    Modern Retreat - Spectacular View Home Above Dry Creek Valley1 / 24
    (18)Very good
    6.0 miles from Chalk Hill Winery
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Skiing: Property Is In A Ski Resort
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    Healdsburg, Sonoma County
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    Downtown Healdsburg Loft - (30 day minimum rentals only)1 / 19
    (4)Excellent
    6.3 miles 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 / 30
    (38)Excellent
    9.6 miles from Chalk Hill Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    A redwood retreat in the heart of Sonoma County wine country (w/ Fiber Internet)1 / 30
    (18)Very good
    7.6 miles from Chalk Hill Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Spectacular view of Dry Creek Valley1 / 24
    (1)Excellent
    7.1 miles from Chalk Hill Winery
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Dry Creek Valley Home and Vineyard1 / 23
    (41)Excellent
    9.6 miles from Chalk Hill Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Entire Resort Villa *Pool-Spa-Tennis-Wine-Dine*1 / 30
    (8)Excellent
    3.6 miles from Chalk Hill Winery
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    Safe Retreat: Bicyclists, Birders, Wine Lovers, River Revelers Welcome!1 / 14
    (82)Excellent
    7.3 miles from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Beautiful Studio Getaway in the Heart of Wine Country1 / 12
    (71)Excellent
    7.2 miles from Chalk Hill Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    luxuriously appointed new large guest suite in a landmark Victorian1 / 18
    (56)Excellent
    7.2 miles from Chalk Hill Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    The Cabin on Fitch Mountain1 / 30
    (40)Very good
    4.7 miles from Chalk Hill Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Tanda Tula, Wine Country Sanctuary1 / 28
    (110)Excellent
    11.7 miles from Chalk Hill Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Mountain Cottage near Russian River, hiking & downtown, family and pet friendly1 / 27
    5.4 miles from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 3 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 3
    Healdsburg Wine Country Getaway with Panoramic Valley Views -Close 2 downtown1 / 24
    (155)Excellent
    6.8 miles from Chalk Hill Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Modern View Home - Pool, hot tub, large deck, BBQ - 1 mile to Healdsburg Plaza1 / 25
    (32)Excellent
    7.0 miles from Chalk Hill Winery
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    Morning Dew-A Riverfront Healdsburg Home1 / 30
    (26)Very good
    4.8 miles from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 4
    Newly Listed 5BR/5.5BA Gorgeous 17 Acre Estate/Pool/Hot Tub/5 mins - Hburg Plaza1 / 30
    7.4 miles from Chalk Hill Winery
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 10
    Stunning Retreat Overlooking Vineyards w/ Pool, Hot Tub & Guest Suite1 / 30
    5.0 miles from Chalk Hill Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Lovely Mid Century Home in Healdsburg1 / 20
    6.0 miles from Chalk Hill Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 4
    Coppola by AvantStay | Explore The Wineries Near This Gorgeous Healdsburg Home!1 / 30
    3.8 miles from Chalk Hill Winery
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Modern Vineyard Farmhouse - Close to Downtown Healdsburg - 4 BD/4 Ensuite Baths1 / 14
    6.8 miles from Chalk Hill Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 4
    Private Healdsburg Retreat Close to Plaza , with River Access.1 / 19
    4.9 miles from Chalk Hill Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Heavenly Hideaway on the Healdsburg Plaza1 / 30
    5.8 miles from Chalk Hill Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Healdsburg Gem! 3BR Pool & Tennis Court1 / 23
    8.4 miles from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    5 BEDROOM 6 1/2 BATH LUXURY HOME ON 3+ ACRES, 5 MIN TO SQUARE1 / 30
    (73)Excellent
    7.3 miles from Chalk Hill Winery
    5 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 5 Bedrooms, 7 Bathrooms, Sleeps 12
    Stay surrounded by Fitch Mountain Park and Open Space Preserve.1 / 14
    (8)Very good
    4.7 miles from Chalk Hill Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Stunning Healdsburg House with Vineyard Views1 / 18
    9.5 miles from Chalk Hill Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 2 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 2
    Great outdoor space, fire pit & gourmet kitchen minutes from downtown Healdsburg1 / 15
    6.0 miles from Chalk Hill Winery
    2 Bedrooms, 1 Bathroom, Sleeps 2 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 2
    Beautiful Mountain Top Retreat (MTR) less than 10 mins from downtown Healdsburg!1 / 30
    (93)Excellent
    5.0 miles from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Peaceful Resort Setting , Healdsburg: Pool, Hot tub, Firepit, 8 Mins to Plaza!1 / 26
    7.6 miles from Chalk Hill Winery
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Hidden Oasis ~ a Private Luxury Home in Healdsburg1 / 22
    6.8 miles from Chalk Hill Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Healdsburg Studio - Vineyard Views!1 / 8
    9.5 miles from Chalk Hill Winery
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    • Internet Access
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    Healdsburg, Sonoma County
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 1
    Santini Farmhouse -- Beautiful Italian style Villa, Hot Tub, Vineyard Views1 / 30
    (14)Excellent
    13.0 miles from Chalk Hill Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Skiing: Property Is In A Ski Resort
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    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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