Photo by Jennifer Hill

Chalk Hill Vacation Rentals

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Vacation Rentals in Chalk Hill

Cottage home near the Russian River; county parks; numerous wineries

10.0 out of 10, Exceptional, (92)
"Property was perfect for me while I was taking care of my grandchildren"
Cottage home near the Russian River; county parks; numerous wineries

Chalk Hill Cottage Close to Wineries

9.8 out of 10, Exceptional, (29)
"Location is excellent, property is clean and quiet, and hosts were very responsive. This is our second time at this cottage and look forward to staying here again. "
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

Gable by AvantStay | Beautiful 3.5 Acre Oasis w/ Gorgeous Views, Pool & Hot Tub

9.2 out of 10, Wonderful, (9)
"Great spot to get away with friends for a long weekend of relaxation and no responsibilities. Beds were comfortable and everyone had plenty of space. Our one bit of feedback would be having a better light above the dining room table in the evening. "
Gable by AvantStay | Beautiful 3.5 Acre Oasis w/ Gorgeous Views, Pool & Hot Tub

Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella

10.0 out of 10, Exceptional, (59)
"Villa Montebella is a wonderful place for a large group. Our families stayed at the Villa over the Thanksgiving Holiday week to celebrate our Daughter’s Napa Wedding. The pictures are accurate, but do not do the property justice. The place is Stunning! There are many comfortable and secluded bedrooms and facilities. The wine cave was amazing and we hired Chef Adair for a special rehearsal dinner there. We have an active group and took advantage of the many amenities. The media room was perfect...
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella

Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!

9.8 out of 10, Exceptional, (299)
"JuJuBe, the house we stayed in for our getaway, was warm and cozy, efficient and well appointed in all things, including kitchen utensils, linens, small appliances, and the like. We stayed during the "atmospheric river" storm and watched the Russian River just down from us rise and swell, yet we were happy in the warmth of the house and always felt quite safe. Great communication with the owner. We'd like to go back when we can take advantage of the available kayaks and outdoor deck. Really a...
Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!

Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard

9.8 out of 10, Exceptional, (410)
"We absolutely adore this property – this has to be our ninth or 10th time back to it. Wonderful home comforts and amazing views— the family history is the cherry on the top."
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard

Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

10.0 out of 10, Exceptional, (220)
"Great place and good location to host 4 couples to celebrate our 50th birthdays. Thank you!"
The price is CA $2,369
CA $3,027 total
includes taxes & fees
Dec 29 - Dec 30
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

Upscale Riverfront Magnificent Views & Hot Tub In Sonoma County Wine Country

10.0 out of 10, Exceptional, (114)
"We spent Thanksgiving at Riverfront and it was perfect! The house was very clean and well stocked in every room. The decks with the view of the Russian River are amazing."
Upscale Riverfront Magnificent Views & Hot Tub In Sonoma County Wine Country

Casa Loma - THE best Napa Valley Views at an amazing, modern 35 acre estate

10.0 out of 10, Exceptional, (124)
"This house has everything and comes well stocked! Love that each bedroom has a king bed and its own bathroom! It’s perfect for groups! The kitchen was well stocked with platters, drink ware, bar essentials, etc. Also, the views are spectacular! We loved our stay! "
Casa Loma - THE best Napa Valley Views at an amazing, modern 35 acre estate

Wine Country Harvest Vacation Home

9.8 out of 10, Exceptional, (67)
"Very niche home with plenty of space inside and out. Lots of space to gather. Convenient location close to grocery shopping and restaurants. "
Wine Country Harvest Vacation Home

Wine Country Getaway

10.0 out of 10, Exceptional, (16)
"We enjoyed our stay in wine country at this place. The house was very clean and well equipped. The beds were very comfortable. The photos accurately depict the openness of the interior. The patio provides a comfortable and inviting extra space. If we are back in the area, we would stay here again."
The price is CA $431
CA $946 total
includes taxes & fees
Dec 31 - Jan 1, 2025
Wine Country Getaway

New Modern House in Sonoma Valley's Best Area

10.0 out of 10, Exceptional, (236)
"Loved this little get-away in an amazing location! Driving up country roads with red and gold vineyards on your right and left in autumn was amazing. And yet, so close to all the best Sonoma wineries!!! The house itself was thoughtfully decorated, with all you need for a wonderful Sonoma escape. We will definitely be back!!!"
New Modern House in Sonoma Valley's Best Area

The St. Helena House - Within Walking Distance To Downtown. Permit # PL23-018

10.0 out of 10, Exceptional, (223)
"Our family stayed at the St. Helena House while attending a memorial. The house exceeded our expectations. It was beautifully decorated, comfortable, and homey with many wonderful nooks to read, views of the vineyards out of every window, and a beautiful well stocked kitchen. The beds were very comfortable. The bathrooms were fine with fluffy towels and plenty of hot water with good water pressure in the showers. The owner was very welcoming and available for any questions. It rained all...
The St. Helena House - Within Walking Distance To Downtown. Permit # PL23-018

COZY Bungalow--Dog-Friendly—Perfect for Couples!!!

9.6 out of 10, Exceptional, (157)
"the bungalow is charming and cozy and very well appointed. Our dog enjoyed the fenced yard and we all enjoyed our short walks to the water’s edge and harbor. Pamela was a gracious host with good recommendations for restaurants in Bodega Bay. We will be returning in the near future. Johanna"
COZY Bungalow--Dog-Friendly—Perfect for Couples!!!

Beautiful 3,000 SF Castle in the Vineyards

9.8 out of 10, Exceptional, (200)
"What a wonderful place to get away. Michael, the host was so friendly and told us the history of the castle. This was a four day getaway with friends and we would love to go back as soon as possible. The home was warm and cozy very unique. The amenities were perfect. first class beddings something you would expect in a five star hotel. Great kitchen with everything you can possibly need to prepare a meal.. We can’t wait to go back!"
Beautiful 3,000 SF Castle in the Vineyards

Valley of the Moon Getaway

10.0 out of 10, Exceptional, (220)
"Great outdoor space with great views"
Valley of the Moon Getaway

Romantic King Bed Studio ~ BEST VIEWS on Bodega Bay - We're right on the water!

9.4 out of 10, Exceptional, (320)
"This place is truly lovely. Marine life is all around you. Views are breathtaking and the Boat House restaurant is practically next door. (Delicious) We enjoyed our stay so much. Very comfortable bed and every need was easily met. This place is absolutely beautiful!!! "
The price is CA $481
CA $943 total
includes taxes & fees
Jan 1 - Jan 2, 2025
Romantic King Bed Studio ~ BEST VIEWS on Bodega Bay - We're right on the water!

A Stylish Getaway In The Heart Of Sonoma Wine Country

10.0 out of 10, Exceptional, (152)
"Enjoyed my 45th birthday in Napa Valley! The place and host were great! Host even let us know about the coffee maker being a drip and not keurig beforehand. I do think it’s a bit tight for 8. Two of the beds are small. Recommend an air mattress if you have more than 7. "
A Stylish Getaway In The Heart Of Sonoma Wine Country

Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

10.0 out of 10, Exceptional, (56)
"Our stay at this VRBO property was absolutely fantastic – truly a 10/10 experience! From the moment we walked in, it was clear that the home was designed with guests in mind. It didn’t feel like we were staying in someone else’s personal space; instead, it felt like a beautifully curated retreat made just for us. Every detail was thoughtfully considered. The house was spotless and had all the important amenities you’d want in a home away from home – a well-equipped kitchen, comfortable beds,...
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
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.
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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, (1010)
"Everything was good except the breakfast was a little disappointing. "
The price is CA $162
CA $185 total
includes taxes & fees
Jan 3 - Jan 4, 2025
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, (793)
"Everything was great no issues at all"
The price is CA $142
CA $162 total
includes taxes & fees
Dec 29 - Dec 30
Holiday Inn Windsor Wine Country, an IHG Hotel

The Sandman Hotel

3.0 star property
8.2 out of 10, Very good, (1988)
"Clean rooms, quiet"
The price is CA $115
CA $133 total
includes taxes & fees
Jan 5 - Jan 6, 2025
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.