Photo by Jennifer Hill

Holiday Homes in Chalk Hill

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Featured Holiday Homes in Chalk Hill and around

Love Shack private retreat

9.0 out of 10, Wonderful, (2)
"Natural light, high ceilings, ac, good WiFi and tv, great location, thoughtful host. "
The price is โ‚ฌ192
includes taxes & fees
16 Sept - 17 Sept
Love Shack private retreat

Vineyard Oasis: Luxury Home in the Heart of Sonoma.

10.0 out of 10, Exceptional, (6)
"Great place in a beautiful setting. Looking forward to staying here again during the next trip."
Vineyard Oasis: Luxury Home in the Heart of Sonoma.

Cobb Mountain Chalet King Size Suite

9.8 out of 10, Exceptional, (21)
"Perfect place to stay, nice and cozy!"
The price is โ‚ฌ127
includes taxes & fees
1 Sept - 2 Sept
Cobb Mountain Chalet King Size Suite

Garden house with gas fireplace

10.0 out of 10, Exceptional, (1)
"We were not originally planning on staying in Middletown but were pleasantly surprised on arrival. The Garden House is very comfortable and convenient to many things in town. Linda, our host had special little touches that made the stay relaxing. Number one the shower is amazing! I looked forward to it every evening the pressure and hot water is perfect and the quality shampoos and soaps provides smelled wonderful! The kitchen is well stocked if you are cooking during your stay. And there is...
The price is โ‚ฌ193
includes taxes & fees
15 Sept - 16 Sept
Garden house with gas fireplace

Wineries & Wine: A Comforting Getaway in Wine Country

9.4 out of 10, Exceptional, (21)
"Great location, apartment and host, highly recommend! "
Wineries & Wine: A Comforting Getaway in Wine Country

Glen Ellen Retreat #1 Hot Tub and King Beds

10.0 out of 10, Exceptional, (67)
"Itโ€™s our third time staying in Glenn Ellen for memorial weekend at this property. Just love it here, and so close to everything. The house is perfectly located, clean, and has everything you need to relax and have a good time!"
The price is โ‚ฌ347
includes taxes & fees
8 Sept - 9 Sept
Glen Ellen Retreat #1 Hot Tub and King Beds

Zegarra Estate

5.0 star property
The price is โ‚ฌ2,154
includes taxes & fees
6 Sept - 7 Sept
Zegarra Estate

Peaceful, charming, cottage in wine country. Beautiful yard!

10.0 out of 10, Exceptional, (3)
"Clean, tastefully decorated in vintage style. Delightful home"
The price is โ‚ฌ269
includes taxes & fees
2 Sept - 3 Sept
Peaceful, charming, cottage in wine country. Beautiful yard!

Charming Wine Country Getaway: Cozy Hot Tub, BBQ, & Mini Golf Fun

9.8 out of 10, Exceptional, (53)
"It was just want I needed for what I was looking for. "
Charming Wine Country Getaway: Cozy Hot Tub, BBQ, & Mini Golf Fun

Lovely Russian River Bungalow-2BR 1 BA New Remodel

10.0 out of 10, Exceptional, (2)
"Great accommodations and convenient location to Santa Rosa, Sebastopol, etc. Impeccably clean and completely remodeled. Nice outdoor area with grill, fire pit, ping pong table and seating for end of day chilling. All kitchen amenities including coffee for am wake-up. Water pressure in shower was amazing. Road up to house is a bit gnarly the first time up before you get your bearings. All check in information available a day in advance. Would definitely be back for another stay."
Lovely Russian River Bungalow-2BR 1 BA New Remodel

2 Hidden Wine Country Gem Upstairs Unit

9.6 out of 10, Exceptional, (19)
"This was a beautiful place to stay. Owner was very accommodating. The place was much larger than I expected. I would definitely recommend a stay here."
2 Hidden Wine Country Gem Upstairs Unit

Russian River Retreat with Hot Tub, BBQ, & Deck

3.5 star property
10.0 out of 10, Exceptional, (3)
"We had a great time visiting the Russian River Valley. This property was as advertised and very comfortable. We had plenty of space and really enjoyed the kitchen, back deck, and hot tub. We had a toddler with us and found the place to be relatively toddler friendly, just had to hide some breakables and barricade the stairs, but she had a great time! Our only complaint was the level of road noise, but that probably comes with any property that is along River Road. "
Russian River Retreat with Hot Tub, BBQ, & Deck

Glen Ellen Retreat #2 King Beds

10.0 out of 10, Exceptional, (147)
"The place was great! Great location, nicely decorated, everything was wonderful-no complaints. "
The price is โ‚ฌ345
includes taxes & fees
2 Sept - 3 Sept
Glen Ellen Retreat #2 King Beds

Serene Retreat with Hot Tub - Fire Pit - Deck

10.0 out of 10, Exceptional, (2)
"The house is so perfect. All the amenities you need and a fire pit and hot tub. Decks to sit on and fencing for privacy. the location of the house and the maintenance of the house was perfect and immaculate. We had one issue and after a quick text, a handyman was there within a few hours. Bedding and furniture was so comfortable. Absolutely quiet at night and the morning. Only one minor drawback. The neighbors were always allowing their dog to run to our car and the dog also followed me down the...
Serene Retreat with Hot Tub - Fire Pit - Deck

Tangerine Cottage spacious home

Tangerine Cottage spacious home

๐‘ณ๐’–๐’™๐’–๐’“๐’š ๐‘ท๐’“๐’Š๐’—๐’‚๐’•๐’† ๐‘ฌ๐’”๐’•๐’‚๐’•๐’† ๐’‚๐’• ๐’๐’๐’†๐’๐’๐’‚ ๐‘ฝ๐’Š๐’๐’†๐’š๐’‚๐’“๐’….๐‘ท๐‘ถ๐‘ถ๐‘ณ&๐‘บ๐‘ท๐‘จ!๐‘ฎ๐‘จ๐‘ด๐‘ฌ๐‘น๐‘ถ๐‘ถ๐‘ด!

9.6 out of 10, Exceptional, (62)
"Great location next to some awesome wineries. Great place to relax after a day of wine tasting!"
๐‘ณ๐’–๐’™๐’–๐’“๐’š ๐‘ท๐’“๐’Š๐’—๐’‚๐’•๐’† ๐‘ฌ๐’”๐’•๐’‚๐’•๐’† ๐’‚๐’• ๐’๐’๐’†๐’๐’๐’‚ ๐‘ฝ๐’Š๐’๐’†๐’š๐’‚๐’“๐’….๐‘ท๐‘ถ๐‘ถ๐‘ณ&๐‘บ๐‘ท๐‘จ!๐‘ฎ๐‘จ๐‘ด๐‘ฌ๐‘น๐‘ถ๐‘ถ๐‘ด!

Secret Garden: 1BR Oasis, Dog Friendly

9.8 out of 10, Exceptional, (6)
Secret Garden: 1BR Oasis, Dog Friendly

Riverbed House with hot tub

10.0 out of 10, Exceptional, (1)
"I am on a non-profit board with 4 people on it. We needed to get our annual planning for 2025-26 done quickly and the best way to do that was to get away from our day-to-day lives and location.Linda's home is lovely, extremely comfortable and has ideal amenities and is a perfect balance between quiet and easily accessible.We had a great visit! Got a ton accomplished while having a great time. We truly felt relaxed even though we were busy nearly the whole time!Thank you so much for making us...
Riverbed House with hot tub

Casa Bella Estate in Wine Country w/ New Pool!

9.6 out of 10, Exceptional, (130)
"Great place to celebrate family members birthdays and Motherโ€™s Day. Excellent location in Sonoma County close to wineries and easy access to SFO and Santa Rosa Airports. Walking distance to a great coffee shop and two wine tasting rooms. Nice large fenced area with pool, jacuzzi, outdoor grill and gathering area. We also enjoyed the covered front porch for relaxing and enjoying the outdoors."
The price is โ‚ฌ3,661
includes taxes & fees
20 Sept - 21 Sept
Casa Bella Estate in Wine Country w/ New Pool!

Charming Wine Country Home w/Hot Tub near Downtown

9.6 out of 10, Exceptional, (11)
"This house was clean, quaint and its location was perfect."
Charming Wine Country Home w/Hot Tub near Downtown
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

Top Chalk Hill Hotel Reviews

Find out more about Chalk Hill

Find out more about Chalk Hill

Chalk Hill Holiday Homes information

Number of reviews
Accommodation
1069 Holiday Homes
Lowest Price
โ‚ฌ225
Highest Price
โ‚ฌ1,007

Explore a world of travel with Expedia

Explore a world of travel with Expedia