Photo by Jennifer Hill

Chalk Hill Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Chalk Hill

Cottage home near the Russian River; county parks; numerous wineries
10.0 out of 10, Exceptional, (89)
"Great house, no issues. "
Cottage home near the Russian River; county parks; numerous wineries
Chalk Hill Cottage Close to Wineries
9.8 out of 10, Exceptional, (24)
"The cottage is very nice and well appointed, with all the needed amenities and more! Very convenient location to visit local wineries and the town of Healdsburg. It was very easy to communicate with our hosts as well. We had a great stay!"
Chalk Hill Cottage Close to Wineries
Stunning Home with Pool, Hot Tub, Decks, & Gourmet Kitchen - Close to Wineries
9.2 out of 10, Wonderful, (88)
"Cleanliness could have been better ( lots of cobwebs and dead flies in the tub) but we enjoyed the property."
Stunning Home with Pool, Hot Tub, Decks, & Gourmet Kitchen - Close to Wineries
Oceanfront - Hot Tub - Newly Remodeled Cottage
9.8 out of 10, Exceptional, (344)
"Breathtaking views and lovely house! Sunsets from the hot tub were my favorite!"
Oceanfront - Hot Tub - Newly Remodeled Cottage
COZY Bungalow--Dog-Friendly—Perfect for Couples!!!
9.6 out of 10, Exceptional, (149)
"Great little private bungalow perfect for couples as advertised. We gad a great stay here and will be staying here again. "
COZY Bungalow--Dog-Friendly—Perfect for Couples!!!
Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!
9.8 out of 10, Exceptional, (287)
"Lovely cabin. We enjoyed our stay very much. The river view was very relaxing and we enjoyed the privacy. "
Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
10.0 out of 10, Exceptional, (213)
"Todd's home was lovely, conveniently located, and had absolutely everything we needed for a comfortable stay. Would stay again!"
The price is AU$3,105
includes taxes & fees
3 Nov - 4 Nov
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard
9.8 out of 10, Exceptional, (394)
"We had the best time celebrating our one year anniversary over Labor Day weekend at Aftermath. We were very excited that the property was pet friendly so we could bring our best boy, Gunther, with as well!! The views from house are breathtaking and we loved being able to walk to the beach to play ball with Gunther. Our favorite part was enjoying the sunsets from the hot tub after dinner. Very clean, well stocked and the perfect location. We can’t wait to come back and are already planning our...
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella
10.0 out of 10, Exceptional, (55)
"We had a wonderful stay. The property is gorgeous and the house was great for a group with places for everyone to be together or separate when needed. We only have a few recommendations. First, the driveway is quite steep and curvy. A caution on that especially if you drive a larger vehicle as we did. We never could get the hot tub to heat up, even after contacting the host. Instructions for that were not in the guest book. Even though the host walked us through it, having it written down would...
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella
New Modern House in Sonoma Valley's Best Area
10.0 out of 10, Exceptional, (227)
"Enjoyed staying at this property. So tastefully decorated. Loved the deer and wild turkeys roaming around the grounds. "
New Modern House in Sonoma Valley's Best Area
Harbor Cutie, Family Friendly, Nearby All Attractions, Playhouse & Outdoor Fun
9.8 out of 10, Exceptional, (191)
"Wonderful and close to everything Bodega Bay! Attentive and friendly host"
The price is AU$914
includes taxes & fees
21 Oct - 22 Oct
Harbor Cutie, Family Friendly, Nearby All Attractions, Playhouse & Outdoor Fun
Stunning Views of CA Coast : Beautifully Remodeled Home
9.8 out of 10, Exceptional, (313)
"Comfortable living room, nice sound system (bring your own tunes), well equipped kitchen. We had a mix of sunny and foggy days, spent most of the time relaxing in the house. Quiet neighborhood. Everything as described in the listing accurate. "
Stunning Views of CA Coast : Beautifully Remodeled Home
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
10.0 out of 10, Exceptional, (207)
"William's property was a spectacular property that sits literally above the clouds (at least the bucolic cloudline in the morning that blankets the valley floor vineyards). So much space to enjoy the outside (from swings, to pickleball/basketball courts, to hikes, to the pool), and a peaceful and welcoming inside. William was also a wonderful host - very responsive and kind. 10 out of 10."
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
4.5 Bedrooms, 3 Baths, 2 Kitchens, 180 degree views and a 'Man Cave'
9.2 out of 10, Wonderful, (156)
"The house has lots of games and cooking supplies you will need. Hot tub was nice. The location is perfect. You can walk to the beach. I would not count the women’s cave near the hot tub as additional bedding to sleep. It looks like people have been using it for their dogs to sleep. However, there is more then enough space to add air mattress on the floor. We had a great time. And the property is perfect for a large family or group of friends."
4.5 Bedrooms, 3 Baths, 2 Kitchens, 180 degree views and a 'Man Cave'
Charming Country Home Nestled In Kenwood Village the heart of the wine country.
10.0 out of 10, Exceptional, (176)
"Two couples stayed at this charming home. The beds were comfortable. The location was great for Sonoma wine tastings, and there were several walkable places to grab a quick bite. We would definitely stay here again."
Charming Country Home Nestled In Kenwood Village the heart of the wine country.
Bodega Bay on the Edge of Pacific Ocean
9.6 out of 10, Exceptional, (112)
"My family and I had a lovely stay at this cozy Bodega Bay home. The house had everything we needed and the host was so kind and communicative. The dunes and beach are a very short walk just out the back door. We thoroughly enjoyed our stay and highly recommend!"
Bodega Bay on the Edge of Pacific Ocean
Waterfront 2 bed 2 bath with the BEST VIEWS
9.8 out of 10, Exceptional, (314)
"Loved sitting on the deck, which is right over the water, watching all the wildlife in and around the water. We felt very at home the minute we walked in. It's minutes from so many beaches and places to explore. Steve and Krista are wonderful host and are always available if you have questions. As many have said the driveway is a little tricky to maneuver but if you follow the instructions exactly as worded you will have no problem. Would definitely stay again! "
The price is AU$989
includes taxes & fees
6 Oct - 7 Oct
Waterfront 2 bed 2 bath with the BEST VIEWS
Wildwood Gardens Scenic Rustic Vacation Retreat on the River
9.6 out of 10, Exceptional, (177)
"We enjoyed our stay at the property. The only downside was the lack of hot water in the shower. Otherwise nice!"
Wildwood Gardens Scenic Rustic Vacation Retreat on the River
Spacious Yet Cozy Bodega Bay Experience!
8.8 out of 10, Excellent, (226)
"We recently enjoyed a stay at a rustic cottage by the sea, and it was a delightful experience overall. The cozy atmosphere made us feel right at home, and we appreciated the thoughtful touches, like Kleenexes in every room. The well-equipped spice rack was another pleasant surprise, making it easy to whip up meals during our stay. However, there were a few drawbacks to note. We discovered some black mold in the farthest bedroom, which was concerning, and one of the beds was unfortunately quite...
Spacious Yet Cozy Bodega Bay Experience!
1 Block To St. Helena Main Street Shops-Restaurants! Avail Oct 6-11,15-16,Nov3-7
10.0 out of 10, Exceptional, (238)
"Such a beautiful property!! The house is immaculate and exactly as pictured. The kitchen, bathrooms and laundry are well stocked with everything you could need. The furniture and beds are modern and very comfortable. The location is on a quiet residential street only 1 block from the Main St in St Helena where all the fabulous restaurants and shopping are located. We were able to walk to dinner most nights. The backyard and landscaping are lush and private. We will definitely book again on our...
1 Block To St. Helena Main Street Shops-Restaurants! Avail Oct 6-11,15-16,Nov3-7
Don't see what you're looking for?
See all available properties in Chalk Hill
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Chalk Hill you may be interested in

Holiday Inn Express® Windsor Sonoma Wine Country, an IHG Hotel
2.5 star property
9.0 out of 10, Wonderful, (1001)
"Always a pleasure staying at this property. Conrad was very friendly along with the person that helped us check in. "
The price is AU$257
includes taxes & fees
1 Nov - 2 Nov
Holiday Inn Express® Windsor Sonoma Wine Country, an IHG Hotel
Holiday Inn Windsor Wine Country, an IHG Hotel
3.0 star property
9.0 out of 10, Wonderful, (693)
"Nice to have a restaurant on site. Really nice fitness center and pool as well."
The price is AU$206
includes taxes & fees
3 Nov - 4 Nov
Holiday Inn Windsor Wine Country, an IHG Hotel
The Sandman Hotel
3.0 star property
8.2 out of 10, Very good, (1910)
"We have stayed at this hotel several times before. Always meets our needs as we visit family. Sad that breakfast on site has gone and our room had no desk - else all good"
The price is AU$160
includes taxes & fees
13 Oct - 14 Oct
The Sandman Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.