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Holiday Homes near Chalk Hill Winery

10300 Chalk Hill Rd, Healdsburg, California 95448-9558
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    All 84 Rentals in Healdsburg
    7.1 kilometres from Chalk Hill Winery
    Studio, 3 Bathrooms, Sleeps 10 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
    4.4 kilometres from Chalk Hill Winery
    5 Bedrooms, 4 Bathrooms, Sleeps 12 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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    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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    • Cable/satellite TV
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    • Grill
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    • Private Outdoor Pool (Unheated)
    • Patio
    • Hot Tub
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 October 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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Upscale, Modern four bedroom, three bath home1 / 20
    (5)Very good
    5.5 kilometres from Chalk Hill Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    Reviewed 23 August 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 11 September 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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    7.1 kilometres from Chalk Hill Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Terrace
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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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    7.5 kilometres from Chalk Hill Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    • Mountain Views
    • Housekeeping Included
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    Pet friendly
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    Smoking allowed
    About this property
    Buena Vista is a Wine Country getaway on the Russian River with Spectacular Views just a short drive 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...
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    7.8 kilometres from Chalk Hill Winery
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
    Suitability
    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
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
    7.7 kilometres from Chalk Hill Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    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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    Pet friendly
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    10.2 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
    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
    12.5 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
    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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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    • 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
    Holiday Rental House - 4 Bedrooms, 7 Bathrooms, Sleeps 8
    Dry Creek Valley Vineyard Home1 / 36
    (29)Excellent
    19.7 kilometres from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Beautiful Views!  Dry Creek Valley Retreat with Deck & Pool, 5 min to Healdsburg1 / 46
    (45)Excellent
    13.3 kilometres from Chalk Hill Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
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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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    • Patio
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    Pet friendly
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    6.2 kilometres from Chalk Hill Winery
    3 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
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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 Healdsburg - Pets Welcome1 / 20
    (29)Excellent
    12.7 kilometres from Chalk Hill Winery
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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
    Dry Creek Valley Home and Vineyard1 / 24
    (27)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
    Peaceful Estate With Views, Incredible Outdoor Space & Only 4 Minutes to Town1 / 23
    (22)Excellent
    13.6 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
    (34)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 / 44
    (50)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
    Safe Retreat: Bicyclists, Birders, Wine Lovers, River Revelers Welcome!1 / 14
    (62)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
    Bunkhouse at Side Road Farm charming one bedroom cottage1 / 35
    (10)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
    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
    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
    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 - 30 day and 4 & 6 night retreats.1 / 47
    (14)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
    luxuriously appointed new large guest suite in a landmark Victorian1 / 21
    (29)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
    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
    Spectacular View Estate 5min Away1 / 45
    (17)Excellent
    14.2 kilometres from Chalk Hill Winery
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
    Enjoy the Sunset from Upscale Home Among Vineyards — short walk to Healdsburg1 / 48
    (49)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 / 26
    (17)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
    River View - Riverfront Getaway in Healdsburg - Hot Tub, Kayaks, River Access1 / 32
    (51)Excellent
    8.7 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
    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
    Redwood River House- Peaceful Riverfront Cottage minutes from Downtown1 / 29
    (31)Very good
    8.8 kilometres from Chalk Hill Winery
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    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
    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
    (63)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 / 22
    (6)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 / 21
    (19)Very good
    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
    (7)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
    (9)Excellent
    7.4 kilometres from Chalk Hill Winery
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Modern Home: Private Hilltop, Views, Pool & Spa  ~  2-6 Guests1 / 38
    (65)Excellent
    10.1 kilometres from Chalk Hill Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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