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Chalk Hill Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Chalk Hill vacation rentals

A balcony with wicker furniture and a glass table, overlooking a scenic landscape during sunset.

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)
"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.
$387 nightly
The price is $428
Oct 29 - Oct 30
Total with taxes and fees
Vineyard View Retreat • Fire Pit • Wine Tasting Perks
A wooden sauna structure with a bench inside, a small pool, and a potted plant outside.

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.
$886 nightly
The price is $996
Nov 1 - Nov 2
Total with taxes and fees
Sauna, Cold Plunge & Fire Pit Near Wineries
A room with a brown sofa, two wicker chairs, a small table, and a lamp.

3. Hideaway Cottages

Hideaway Cottages
2.0 star property
Calistoga
$180 nightly
The price is $207
Nov 1 - Nov 2
Total with taxes and fees
Hideaway Cottages
A cozy cabin with a loft bedroom, wooden exterior, and a small balcony.

4. Wildhaven Sonoma Glamping

Wildhaven Sonoma Glamping
1.0 star property
Healdsburg
9.2 out of 10, Wonderful, (138 reviews)
"Nice place to be in with your dog, very good for comfortable stay"
United States
NEERJA
$123 nightly
The price is $140
Oct 29 - Oct 30
Total with taxes and fees
Wildhaven Sonoma Glamping
A single-story cabin with a small porch, situated on a hillside overlooking a body of water and mountains.

5. The Ranch at Lake Sonoma

The Ranch at Lake Sonoma
1.0 star property
Geyserville
9.0 out of 10, Wonderful, (9 reviews)
"Nice camping spot "
United States
Evelyn
$79 nightly
The price is $90
Oct 28 - Oct 29
Total with taxes and fees
The Ranch at Lake Sonoma
A white building with a covered porch, potted plants, and a bicycle.

6. 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
$152 nightly
The price is $170
Oct 28 - Oct 29
Total with taxes and fees
Mandala Springs Wellness Retreat Center
A swimming pool with a slide, a barbecue area, and a wooden deck.

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.
$248 nightly
The price is $279
Oct 28 - Oct 29
Total with taxes and fees
2 Hidden Wine Country Gem Upstairs Unit
A patio area with a stone floor, outdoor seating, and a house in the background.

8. 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
$227 nightly
The price is $242
Nov 16 - Nov 17
Total with taxes and fees
Sebastopol Lux Walk toTown Guest Suite
A beach with a large rock formation, a sandy shore, and a calm sea.

9. The Tiny Tipsy Turtle

The Tiny Tipsy Turtle
Guerneville
10.0 out of 10, Exceptional, (67 reviews)
"Great little place to stay / perfect location in town close to everything / wonderful front patio "
United States
ANTHONY B.
$207 nightly
The price is $221
Nov 10 - Nov 11
Total with taxes and fees
The Tiny Tipsy Turtle
Private kitchen

10. 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.
$316 nightly
The price is $355
Nov 9 - Nov 10
Total with taxes and fees
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
An outdoor patio with wooden chairs and a table, surrounded by greenery and a white pergola.

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

Peaceful, charming, cottage in wine country. Beautiful yard!
Sebastopol
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful, charming cottage in a quiet neighborhood. Close to wineries and food."
United States
Mikaela
$330 nightly
The price is $365
Nov 9 - Nov 10
Total with taxes and fees
Peaceful, charming, cottage in wine country. Beautiful yard!
A covered outdoor deck with a table and chairs, a grill, and a bottle of wine.

12. Cobb Mountain Chalet King Size Suite

Cobb Mountain Chalet King Size Suite
Cobb
9.2 out of 10, Wonderful, (31 reviews)
"Lovely place, very clean, in quiet surroundings."
United States
Brigid
$167 nightly
The price is $184
Nov 2 - Nov 3
Total with taxes and fees
Cobb Mountain Chalet King Size Suite
A small, single-story house with a front porch, a chimney, and a door with a window above it.

13. 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
$376 nightly
The price is $451
Oct 28 - Oct 29
Total with taxes and fees
Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
A wooden structure with a circular entrance, a small table, and a sofa outside a house.

14. Forestville Redwood Escape

Forestville Redwood Escape
Forestville
$436 nightly
The price is $436
Nov 4 - Nov 5
Total with taxes and fees
Forestville Redwood Escape
A spacious living room with a fireplace, wooden flooring, and a cozy seating area.

15. Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA
Santa Rosa
9.8 out of 10, Exceptional, (82 reviews)
"Our stay was pleasant, the place was exceptionally clean and the owners were very helpful."
United States
joanne h.
$410 nightly
The price is $436
Nov 27 - Nov 28
Total with taxes and fees
Wine Country Cottage in downtown Santa Rosa, CA
A wooden interior with a dining area, a bench, and a mirror on the wall.

16. Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.8 out of 10, Exceptional, (29 reviews)
"It was wonderful, we'll be back!"
United States
Jehanne H.
$428 nightly
The price is $481
Oct 28 - Oct 29
Total with taxes and fees
Cozy Riverfront Cabin - Beach Access & Wood Stove
A house with a swimming pool surrounded by lush greenery and a small waterfall feature.

17. Cozy Wine Country Guesthouse with Private Pool & Yard

Cozy Wine Country Guesthouse with Private Pool & Yard
Santa Rosa
10.0 out of 10, Exceptional, (38 reviews)
"Wonderful stay!"
United States
Adam C.
$356 nightly
The price is $356
Oct 28 - Oct 29
Total with taxes and fees
Cozy Wine Country Guesthouse with Private Pool & Yard
A spacious kitchen with a large island, wooden ceiling, and large windows offering a view of the deck.

18. The Cozy Pine Cone . Hot tub- Deck & Grill Forestville

The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
Forestville
10.0 out of 10, Exceptional, (15 reviews)
"Nice place, great location, had everything we needed. Helpful and prompt communication by the host. This was a great base for exploring the area."
United States
Rebecca I.
$385 nightly
The price is $426
Nov 1 - Nov 2
Total with taxes and fees
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
A hallway with white paneling and wooden doors, leading to an outdoor area with greenery.

19. 2BR Bungalow - Russian River & Wine Country

2BR Bungalow - Russian River & Wine Country
Forestville
9.8 out of 10, Exceptional, (22 reviews)
"Nice clean relaxing place to stay near the river! Was perfect for our little weekend getaway."
United States
Greg K.
$361 nightly
The price is $408
Nov 22 - Nov 23
Total with taxes and fees
2BR Bungalow - Russian River & Wine Country
A hot tub on a wooden deck with a view of a forested area.

20. Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK

Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Guerneville
9.4 out of 10, Exceptional, (10 reviews)
"Very unique and charming property. Definitely felt like being in a tree house in the redwoods. We spent most of our time when there sitting on the deck. It was conveniently located to everything we wanted to do - drive to the coast, hike at the state park, and visit nearby restaurants and wineries."
United States
Sherri
$386 nightly
The price is $434
Nov 1 - Nov 2
Total with taxes and fees
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
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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Top Chalk Hill Hotel Reviews

Hyatt Regency Sonoma Wine Country

Hyatt Regency Sonoma Wine Country

10/10 Excellent
"Great hotel. Very clean very spacious room & bathroom!"
Shayla 2-night trip
Posted 1 hour ago
Hyatt Regency Sonoma Wine Country

Find out more about Chalk Hill

Everything you need to know about Chalk Hill vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chalk Hill vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chalk Hill vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chalk Hill vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chalk Hill. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chalk Hill in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $90 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chalk Hill rentals

At Expedia, we put the best Chalk Hill vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chalk Hill rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chalk Hill vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chalk Hill. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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