We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals near Chalk Hill Winery

10300 Chalk Hill Rd, Healdsburg, California 95448-9558
Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    $510 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Travelers to Healdsburg are booking September dates now. Secure your vacation rental today, and have the perfect trip.
    All 74 Rentals in Healdsburg
    Wine Country Home on Chalk Hill - main house + pool house (up to 12 guests)1 / 29
    (4)Very good
    2.7 miles from Chalk Hill Winery
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Limerick Lane / Stunning, Quiet, Contemporary, Single-Level, Eco-Friendly1 / 25
    (3)Excellent
    3.6 miles from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    4.9 miles from Chalk Hill Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    4.8 miles from Chalk Hill Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Mountain Views
    • Internet Access
    • Washer
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    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...
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    5.9 miles from Chalk Hill Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Terrace
    • Patio
    • Air Conditioning
    • Balcony
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    8.0 miles from Chalk Hill Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Internet Access
    • Parking
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    3.7 miles from Chalk Hill Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Grill
    • Parking
    • Patio
    • Air Conditioning
    • Washer
    Suitability
    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...
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    3.6 miles from Chalk Hill Winery
    4 Bedrooms, 7 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 7 Bathrooms, Sleeps 8
    Dry Creek Valley Vineyard Home1 / 36
    (29)Excellent
    12.2 miles from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Patio
    • Parking
    • Internet Access
    • Cable/satellite TV
    • Hot Tub
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Beautiful Views!  Dry Creek Valley Retreat with Deck & Pool, 5 min to Healdsburg1 / 46
    (45)Excellent
    8.2 miles from Chalk Hill Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Parking
    • Internet Access
    • Washer
    • DVD Player
    • Central Heating
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Save time - get the best Healdsburg rentals sent straight to your email!
    Get the List
    Crossroads Vineyard:  In the Heart of Healdsburg Wine Country1 / 23
    (88)Excellent
    7.7 miles from Chalk Hill Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Balcony
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Hot Tub
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    3.8 miles from Chalk Hill Winery
    3 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • Internet Access
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 5 Bathrooms, Sleeps 10
    Enjoy a Slice Of Country--Two miles to Downtown Healdsburg - Pets Welcome1 / 20
    (31)Excellent
    7.8 miles from Chalk Hill Winery
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Patio
    • Washer
    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Breathtaking Dry Creek Estate - Modern, Spacious, Luxury!1 / 33
    (5)Excellent
    9.0 miles from Chalk Hill Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Patio
    • Hot Tub
    • Washer
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    8.0 miles from Chalk Hill Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Hot Tub
    • Patio
    • Parking
    • Washer
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Spectacular view of Dry Creek Valley1 / 26
    (1)Excellent
    7.0 miles from Chalk Hill Winery
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Parking
    • Internet Access
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Dry Creek Valley Home and Vineyard1 / 24
    (27)Excellent
    9.6 miles from Chalk Hill Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Patio
    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Peaceful Estate With Views, Incredible Outdoor Space & Only 4 Minutes to Town1 / 23
    (22)Excellent
    8.4 miles from Chalk Hill Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Cable/satellite TV
    • Washer
    • Internet Access
    • DVD Player
    • Patio
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Superb Healdsburg Location, Spectacular Views, Minutes to Town1 / 49
    (34)Excellent
    5.4 miles from Chalk Hill Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • DVD Player
    • Air Conditioning
    • Patio
    • Internet Access
    • Parking
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    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 / 44
    (50)Very good
    4.8 miles from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Cable/satellite TV
    • Internet Access
    • DVD Player
    • Central Heating
    • Washer
    • Patio
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    List your property for free!
    List your vacation rental where Tripadvisor travelers can find it.
    Add a Listing
    Enchanting Wine Country Villa1 / 24
    (3)Excellent
    3.8 miles from Chalk Hill Winery
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Hot Tub
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    Luxury Vineyard Estate House and Guest House1 / 45
    (73)Excellent
    3.6 miles from Chalk Hill Winery
    5 Bedrooms, 4 Bathrooms, Sleeps 4 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Terrace
    • Air Conditioning
    • Balcony
    • Cable/satellite TV
    • Washer
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 4
    Safe Retreat: Bicyclists, Birders, Wine Lovers, River Revelers Welcome!1 / 14
    (62)Excellent
    7.3 miles from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Patio
    • Internet Access
    • Air Conditioning
    • Hot Tub
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Bunkhouse at Side Road Farm charming one bedroom cottage1 / 35
    (11)Excellent
    5.7 miles from Chalk Hill Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Beautiful Studio Getaway  in the Heart of Wine Country1 / 12
    (36)Excellent
    7.2 miles from Chalk Hill Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    6.9 miles from Chalk Hill Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Washer
    • Cable/satellite TV
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Vineyard Guest House1 / 31
    (17)Excellent
    12.1 miles from Chalk Hill Winery
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    4,700 ft 4 bed & 4 bath ranch, Summer 2020, fully catered plant based retreats1 / 47
    (14)Excellent
    8.8 miles from Chalk Hill Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • Internet Access
    • Housekeeping Included
    • Cable/satellite TV
    • DVD Player
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    luxuriously appointed new large guest suite in a landmark Victorian1 / 21
    (29)Excellent
    7.2 miles from Chalk Hill Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • Patio
    • DVD Player
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    5.9 miles from Chalk Hill Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Parking
    • Internet Access
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Spectacular View Estate 5min Away1 / 45
    (17)Excellent
    8.8 miles from Chalk Hill Winery
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Hot Tub
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 12
    Enjoy the Sunset from Upscale Home Among Vineyards — short walk to Healdsburg1 / 48
    (49)Excellent
    6.5 miles from Chalk Hill Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Air Conditioning
    • Internet Access
    • Washer
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Stunning Mountain Top Estate with View Over Dry Creek Vineyards1 / 28
    (17)Excellent
    12.8 miles from Chalk Hill Winery
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Washer
    • Internet Access
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    River View - Riverfront Getaway in Healdsburg - Hot Tub, Kayaks, River Access1 / 32
    (51)Excellent
    5.4 miles from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Central Heating
    • Parking
    • Cable/satellite TV
    • Internet Access
    • Hot Tub
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Dry Creek Cottage - Healdsburg1 / 6
    (48)Excellent
    7.1 miles from Chalk Hill Winery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Parking
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Redwood River House- Peaceful Riverfront Cottage minutes from Downtown1 / 29
    (31)Very good
    5.4 miles from Chalk Hill Winery
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Internet Access
    • Hot Tub
    • Patio
    • Parking
    • Washer
    • Cable/satellite TV
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Private Wine Country Retreat-Luxury estate, pool, hot tub, 3 miles to town1 / 42
    (38)Excellent
    8.4 miles from Chalk Hill Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Parking
    • Balcony
    • Cable/satellite TV
    • Hot Tub
    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    4.7 miles from Chalk Hill Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Patio
    • Parking
    • Terrace
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Tanda Tula, Wine Country Sanctuary1 / 28
    (73)Excellent
    11.7 miles from Chalk Hill Winery
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • Internet Access
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Creek Front Vineyard, West Dry Creek Healdsburg CA1 / 30
    (6)Excellent
    11.7 miles from Chalk Hill Winery
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • Internet Access
    • DVD Player
    • Cable/satellite TV
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 6 Bedrooms, 7 Bathrooms, Sleeps 12
    Private 3 Bed + Cottage Wine Country Estate With Pool And More1 / 21
    (19)Very good
    7.2 miles from Chalk Hill Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Cable/satellite TV
    • Sauna
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Wine country getaway; stay in a winery1 / 12
    (8)Excellent
    9.5 miles from Chalk Hill Winery
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Parking
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Updated cabin, right on Russian River, amazing views & location!1 / 23
    (9)Excellent
    4.6 miles from Chalk Hill Winery
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • DVD Player
    • Internet Access
    • Washer
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Modern Home: Private Hilltop, Views, Pool & Spa  ~  2-6 Guests1 / 38
    (65)Excellent
    6.3 miles from Chalk Hill Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Patio
    • Internet Access
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Modern Retreat - Spectacular View Home Above Dry Creek Valley1 / 24
    (18)Very good
    5.9 miles from Chalk Hill Winery
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Parking
    • Housekeeping Included
    • DVD Player
    • Air Conditioning
    • Patio
    • Washer
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    Downtown Healdsburg Loft - (30 day minimum rentals only)1 / 19
    (1)Excellent
    6.2 miles from Chalk Hill Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Terrace
    • Cable/satellite TV
    • Washer
    • Patio
    • Parking
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    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
    5.4 miles from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Washer
    • Parking
    • Central Heating
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Luxury Wine Country Home in the Heart of Healdsburg with a Private Pool.1 / 49
    (11)Excellent
    9.7 miles from Chalk Hill Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Cable/satellite TV
    • Patio
    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    A redwood retreat in the heart of Sonoma County wine country.1 / 24
    (7)Excellent
    7.6 miles from Chalk Hill Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Hot Tub
    • Washer
    • Air Conditioning
    • DVD Player
    • Patio
    • Cable/satellite TV
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Healdsburg Bliss House-Sonoma Wine Country Sweeping Panoramic Vineyard Views1 / 14
    (87)Excellent
    6.8 miles from Chalk Hill Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Air Conditioning
    • Washer
    • Internet Access
    • Parking
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    1
    List your property
    Owner log in
    $USD
    United States

    This is the version of our website addressed to speakers of English in the United States. If you are a resident of another country or region, please select the appropriate version of Tripadvisor for your country or region in the drop-down menu.