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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Chalk Hill vacation rentals

Terrace/patio

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

Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Healdsburg
9.8 out of 10, Exceptional, (17 reviews)
"The house was just like advertised. Great location to visit the surrounding area."
United States
David S.
The price is ￥24,885
￥60,111 total
includes taxes & fees
Sep 21 - Sep 22
Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Property grounds

2. Wildflower

Wildflower
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 ￥33,487
￥140,687 total
includes taxes & fees
Sep 16 - Sep 17
Wildflower
Deluxe Cabin, 1 Queen Bed, Patio, Garden View | Laptop workspace, WiFi (free), bed sheets

3. Wildhaven Sonoma Glamping

Wildhaven Sonoma Glamping
1.0 star property
Healdsburg
9.2 out of 10, Wonderful, (132 reviews)
"Nice place to be in with your dog, very good for comfortable stay"
United States
NEERJA
The price is ￥14,125
￥16,103 total
includes taxes & fees
Oct 13 - Oct 14
Wildhaven Sonoma Glamping
Exterior

4. The Ranch at Lake Sonoma

The Ranch at Lake Sonoma
1.0 star property
Geyserville
9.8 out of 10, Exceptional, (6 reviews)
"Nice camping spot "
United States
Evelyn
The price is ￥12,166
￥13,870 total
includes taxes & fees
Sep 13 - Sep 14
The Ranch at Lake Sonoma
Lobby sitting area

5. Sonoma Stonehouse, Wine Country Vibes

Sonoma Stonehouse, Wine Country Vibes
2.0 star property
Santa Rosa
8.0 out of 10, Very Good, (1 review)
"Muy bonito diseño interior en ambos la recepción y el cuarto."
Mexico
Tara
The price is ￥30,906
￥58,124 total
includes taxes & fees
Sep 20 - Sep 21
Sonoma Stonehouse, Wine Country Vibes
Exterior

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

Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
Calistoga
9.8 out of 10, Exceptional, (44 reviews)
"Host, amenities, location….all excellent. "
United States
Amy B.
The price is ￥52,074
￥71,469 total
includes taxes & fees
Sep 13 - Sep 14
Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
TV, fireplace

7. Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries

Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
Northwest Santa Rosa
9.8 out of 10, Exceptional, (76 reviews)
"Great place close to KJ and La Crema wineries!"
United States
Nancy P.
The price is ￥52,995
￥101,213 total
includes taxes & fees
Sep 13 - Sep 14
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
Meeting facility

8. Mandala Springs Wellness Retreat Center

Mandala Springs Wellness Retreat Center
3.5 star property
Cobb
9.0 out of 10, Wonderful, (37 reviews)
"Waterfront cabins were amazing. The location and wildlife were serene, fantastic place to stay."
United States
Carmino
The price is ￥23,756
￥26,487 total
includes taxes & fees
Sep 14 - Sep 15
Mandala Springs Wellness Retreat Center
Outdoor pool, a heated pool

9. Cozy Wine Country Guesthouse with Private Pool & Yard

Cozy Wine Country Guesthouse with Private Pool & Yard
Santa Rosa
10.0 out of 10, Exceptional, (32 reviews)
"Would return again, The space was larger than it looked in photos."
United States
Keriann
The price is ￥48,387
￥54,531 total
includes taxes & fees
Sep 17 - Sep 18
Cozy Wine Country Guesthouse with Private Pool & Yard
Outdoor dining

10. Wine Country Farmhouse with Hot Tub

Wine Country Farmhouse with Hot Tub
Santa Rosa
10.0 out of 10, Exceptional, (74 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 ￥52,227
￥95,053 total
includes taxes & fees
Sep 27 - Sep 28
Wine Country Farmhouse with Hot Tub
Terrace/patio

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

Escape to wine country in your independent cottage in downtown Calistoga
Calistoga
10.0 out of 10, Exceptional, (6 reviews)
"We made the Calistoga CA area our base for our recent trip and the Cottage Grove Inn served as a great place to stay."
United States
Anonymous traveler
The price is ￥47,465
￥65,041 total
includes taxes & fees
Sep 13 - Sep 14
Escape to wine country in your independent cottage in downtown Calistoga
Outdoor dining

12. River View Lodge - Hot Tub and Tastings Included

River View Lodge - Hot Tub and Tastings Included
Healdsburg
9.6 out of 10, Exceptional, (75 reviews)
"View was lovely. The Hot tub was great. Beds were very comfy!"
United States
Julie B.
The price is ￥82,369
￥178,762 total
includes taxes & fees
Sep 21 - Sep 22
River View Lodge - Hot Tub and Tastings Included
Dining

13. Wine Country Getaway

Wine Country Getaway
Mirabel Heights
10.0 out of 10, Exceptional, (33 reviews)
"Great place, would stay again!"
United States
Rachel S.
The price is ￥30,415
￥81,684 total
includes taxes & fees
Sep 13 - Sep 14
Wine Country Getaway
Smart TV

14. Serenity at the Russian River

Serenity at the Russian River
Mirabel Heights
10.0 out of 10, Exceptional, (41 reviews)
"Great hosts. Very accommodating. Clean and beautiful property. Great timely communication with hosts."
United States
Neeraj
The price is ￥27,650
￥78,741 total
includes taxes & fees
Sep 13 - Sep 14
Serenity at the Russian River
Exterior

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

Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed
Calistoga
10.0 out of 10, Exceptional, (4 reviews)
"Property is beautiful rooms are so clean. Service was incredible."
United States
Paul L.
The price is ￥47,465
￥62,737 total
includes taxes & fees
Oct 5 - Oct 6
Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed
A heated pool

16. Farpoint: Heated Infinity Pool, Mountain Views

Farpoint: Heated Infinity Pool, Mountain Views
Santa Rosa
10.0 out of 10, Exceptional, (23 reviews)
"Loved our stay."
United States
Vanessa R.
The price is ￥75,161
￥151,001 total
includes taxes & fees
Sep 14 - Sep 15
Farpoint: Heated Infinity Pool, Mountain Views
Interior

17. Artisan Boho, Equine Too, Farm Fresh Eggs, Spa, Vino & Views!

Artisan Boho, Equine Too, Farm Fresh Eggs, Spa, Vino & Views!
Sebastopol
9.8 out of 10, Exceptional, (7 reviews)
"Well-appointed, very responsive host!"
United States
Sally S.
The price is ￥46,390
￥84,061 total
includes taxes & fees
Sep 28 - Sep 29
Artisan Boho, Equine Too, Farm Fresh Eggs, Spa, Vino & Views!
Studio | Exterior

18. Rouge Cobb Mountain Hotel - Cabin 3

Rouge Cobb Mountain Hotel - Cabin 3
2.0 star property
Cobb
10.0 out of 10, Exceptional, (1 review)
"I love this place. The River was going on. I wish I can go every weekend there.thank you for everything. We appreciate the owner."
United States
JOSELITA
Rouge Cobb Mountain Hotel - Cabin 3
Terrace/patio

19. Private Vineyard Haven with Pool, Hot Tub and Tastings Included

Private Vineyard Haven with Pool, Hot Tub and Tastings Included
Healdsburg
9.8 out of 10, Exceptional, (68 reviews)
"Great location for touring wineries in the area. Very nice accommodations for 2 couples."
United States
Rock R.
The price is ￥136,867
￥258,005 total
includes taxes & fees
Sep 29 - Sep 30
Private Vineyard Haven with Pool, Hot Tub and Tastings Included
Coffee/tea maker, fridge, microwave, oven

20. 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 ￥22,427
￥60,820 total
includes taxes & fees
Sep 21 - Sep 22
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chalk Hill Hotel Reviews

The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

10/10 Excellent
"The rooms were super clean and super spacious and really cute! The staff was helpful during check in. We did have to pay for parking but it was a small added fee and there was plenty of parking. My friend and I spent the first day by the pool and bar. The pool was really clean and the pool area was a nice space to sit down and relax. The free breakfast had everything you could need: coffee eggs waffles cereal potatoes sausages. Everything was good😀"
Alma 2-night trip
Posted less than an hour ago
The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

Find out more about Chalk Hill

Search for holiday rentals in Chalk Hill on Expedia! You can easily find your home rentals, villas, holiday apartments in Chalk Hill using one of the methods below:

  • View our selection of featured holiday rentals in Chalk Hill
  • Use the map to find apartments and other holiday homes in the Chalk Hill neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chalk Hill while they last

Look no further and take a look at our great range of rental properties in Chalk Hill!

Explore a world of travel with Expedia