A group of large hot air balloons, including a yellow one with a face, and a white van with cartoon characters.

Chalk Hill Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chalk Hill vacation rentals

1. Vineyard View Retreat • Fire Pit • Wine Tasting Perks

Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Healdsburg
9.8 out of 10, Exceptional, (19 reviews)
"Great place. Quiet, very clean, close to Healdsburg, grocery stores, etc. Very helpful and nice host. We would definitely stay here again when in the area."
United States
Mark R.
The price is CA $242
CA $544 total
includes taxes & fees
Dec 1 - Dec 2
Vineyard View Retreat • Fire Pit • Wine Tasting Perks

2. Sauna, Cold Plunge & Fire Pit Near Wineries

Sauna, Cold Plunge & Fire Pit Near Wineries
Windsor
10.0 out of 10, Exceptional, (1 review)
"Very accommodating home with all the essentials. Awesome backyard for the dogs, great location and communication. "
United States
Keri S.
The price is CA $301
CA $1,323 total
includes taxes & fees
Nov 10 - Nov 11
Sauna, Cold Plunge & Fire Pit Near Wineries

3. Hideaway Cottages

Hideaway Cottages
2.0 star property
Calistoga
4.0 out of 10, (1 review)
"Old but quaint. No amenities, no updates. Coffee cups looked like thrift shop purchases. Bed was comfortable. Bath shower drained poorly. Too expensive for a 2 star property."
United States
Chris
The price is CA $311
CA $357 total
includes taxes & fees
Nov 17 - Nov 18
Hideaway Cottages

4. Wildhaven Sonoma Glamping

Wildhaven Sonoma Glamping
1.0 star property
Healdsburg
9.2 out of 10, Wonderful, (139 reviews)
"Nice place to be in with your dog, very good for comfortable stay"
United States
NEERJA
The price is CA $129
CA $147 total
includes taxes & fees
Dec 10 - Dec 11
Wildhaven Sonoma Glamping

5. Mandala Springs Wellness Retreat Center

Mandala Springs Wellness Retreat Center
3.5 star property
Cobb
8.8 out of 10, Excellent, (39 reviews)
"Waterfront cabins were amazing. The location and wildlife were serene, fantastic place to stay."
United States
Carmino
The price is CA $203
CA $226 total
includes taxes & fees
Nov 17 - Nov 18
Mandala Springs Wellness Retreat Center

6. The Ranch at Lake Sonoma

The Ranch at Lake Sonoma
1.0 star property
Geyserville
9.0 out of 10, Wonderful, (10 reviews)
"Enjoyed my stay"
United States
Epeli
The price is CA $112
CA $128 total
includes taxes & fees
Nov 10 - Nov 11
The Ranch at Lake Sonoma

7. 2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (32 reviews)
"We enjoyed our stay and would certainly use this rental again if we're ever in the area. "
United States
Glen M.
The price is CA $177
CA $381 total
includes taxes & fees
Nov 16 - Nov 17
2 Hidden Wine Country Gem Upstairs Unit

8. Cozy Wine Country Guesthouse with Private Pool & Yard

Cozy Wine Country Guesthouse with Private Pool & Yard
Santa Rosa
10.0 out of 10, Exceptional, (39 reviews)
"Wonderful stay!"
United States
Adam C.
The price is CA $445
CA $482 total
includes taxes & fees
Nov 10 - Nov 11
Cozy Wine Country Guesthouse with Private Pool & Yard

9. Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA
Santa Rosa
9.8 out of 10, Exceptional, (83 reviews)
"Our stay was pleasant, the place was exceptionally clean and the owners were very helpful."
United States
joanne h.
The price is CA $311
CA $604 total
includes taxes & fees
Nov 10 - Nov 11
Wine Country Cottage in downtown Santa Rosa, CA

10. Private Lofted Downtown Studio

Private Lofted Downtown Studio
Sebastopol
9.8 out of 10, Exceptional, (55 reviews)
"Very cute and luxurious!! We really enjoyed our stay and great proximity to downtown. "
United States
Yvonne L.
The price is CA $337
CA $657 total
includes taxes & fees
Nov 13 - Nov 14
Private Lofted Downtown Studio

11. Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown

Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
Calistoga
9.6 out of 10, Exceptional, (49 reviews)
"We stayed here 15 years ago , same bedspreads and no new updates . We love it for its cozy feeling , and love the peacefulness of staying in Calistoga. We walked across the street for an awesome dinner at Sam’s Social club , walked down the street to shop and cruise around this quaint town . It’s a high price point , but we always enjoy our time there . I worry that if they ever remodel this place , the price point will be more than what it’s worth a night , for which I don’t believe would be...
United States
William
The price is CA $493
CA $648 total
includes taxes & fees
Nov 10 - Nov 11
Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown

12. Escape to wine country in your independent cottage in downtown Calistoga

Escape to wine country in your independent cottage in downtown Calistoga
Calistoga
9.8 out of 10, Exceptional, (8 reviews)
"We absolutely loved our stay! The home was clean, quiet, private, and incredibly convenient. We were especially grateful that the hosts allowed our three dogs, which made this trip extra special. We spent a few days enjoying Calistoga and Napa before taking our sweet pup to UC Davis, and this was the perfect place for us. As empty nesters, we love traveling with our three dogs and hope to stay here again someday!"
United States
Jennifer G.
The price is CA $493
CA $648 total
includes taxes & fees
Nov 10 - Nov 11
Escape to wine country in your independent cottage in downtown Calistoga

13. Wine Country Farmhouse on a Horse Ranch w/ Hot Tub

Wine Country Farmhouse on a Horse Ranch w/ Hot Tub
Santa Rosa
10.0 out of 10, Exceptional, (75 reviews)
"The property was beautiful and the beds were so comfy! The property manager was very friendly and responsive. "
United States
Abigail M.
The price is CA $339
CA $664 total
includes taxes & fees
Nov 10 - Nov 11
Wine Country Farmhouse on a Horse Ranch w/ Hot Tub

14. Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed

Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed
Calistoga
10.0 out of 10, Exceptional, (5 reviews)
"Property is beautiful rooms are so clean. Service was incredible."
United States
Paul L.
The price is CA $493
CA $648 total
includes taxes & fees
Nov 10 - Nov 11
Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed

15. Sebastopol Lux Walk toTown Guest Suite

Sebastopol Lux Walk toTown Guest Suite
Sebastopol
9.4 out of 10, Exceptional, (8 reviews)
"Beautiful place. Bed was extremely comfortable. Overall environment was pleasant. Coffee set up was good for me as a black coffee drinker. We would stay again and would happily recommend it to others."
United States
Brad
The price is CA $178
CA $331 total
includes taxes & fees
Nov 16 - Nov 17
Sebastopol Lux Walk toTown Guest Suite

16. Charming Wine Country Home w/Hot Tub near Downtown

Charming Wine Country Home w/Hot Tub near Downtown
Santa Rosa
9.8 out of 10, Exceptional, (21 reviews)
"Very clean, convenient for our purposes, thank you"
United States
Howard
The price is CA $375
CA $819 total
includes taxes & fees
Nov 10 - Nov 11
Charming Wine Country Home w/Hot Tub near Downtown

17. Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts

Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts
Northwest Santa Rosa
10.0 out of 10, Exceptional, (85 reviews)
"Great Home. Decent value.Didn’t realize the street were gonna be so compacted with houses very small streets"
United States
Melissa M.
The price is CA $424
CA $855 total
includes taxes & fees
Nov 13 - Nov 14
Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts

18. Serenity at the Russian River

Serenity at the Russian River
Mirabel Heights
10.0 out of 10, Exceptional, (44 reviews)
"We had a great stay. The house was clean, the beds were comfy and a very convenient location. Just wish there was an ironing board. I would definitely recommend staying here."
United States
Patricia A.
The price is CA $254
CA $731 total
includes taxes & fees
Nov 12 - Nov 13
Serenity at the Russian River

19. Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Northwest Santa Rosa
9.4 out of 10, Exceptional, (23 reviews)
"very nice space "
United States
kevin c.
The price is CA $153
CA $490 total
includes taxes & fees
Nov 10 - Nov 11
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

20. Modern Country Home Near Downtown & Bike Trail

Modern Country Home Near Downtown & Bike Trail
Sebastopol
10.0 out of 10, Exceptional, (9 reviews)
"Very clean and lots of you nearby"
United States
Santo Q.
The price is CA $282
CA $716 total
includes taxes & fees
Nov 10 - Nov 11
Modern Country Home Near Downtown & Bike Trail
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chalk Hill. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Explore a world of travel with Expedia