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Chalk Hill Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Chalk Hill vacation rentals

A cozy cabin with a loft bedroom, wooden exterior, and a small balcony.

1. Wildhaven Sonoma Glamping

Wildhaven Sonoma Glamping
1.0 star property
Healdsburg
9.2 out of 10, Wonderful, (135 reviews)
"Nice place to be in with your dog, very good for comfortable stay"
United States
NEERJA
$99 nightly
The price is $113
Nov 10 - Nov 11
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.

2. 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
$79 nightly
The price is $90
Oct 11 - Oct 12
Total with taxes and fees
The Ranch at Lake Sonoma
A swimming pool with a slide, a barbecue area, and a wooden deck.

3. 2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (31 reviews)
"We enjoyed our stay and would certainly use this rental again if we're ever in the area. "
United States
Glen M.
$250 nightly
The price is $281
Oct 15 - Oct 16
Total with taxes and fees
2 Hidden Wine Country Gem Upstairs Unit
A white building with a covered porch, potted plants, and a bicycle.

4. Mandala Springs Wellness Retreat Center

Mandala Springs Wellness Retreat Center
3.5 star property
Cobb
8.8 out of 10, Excellent, (38 reviews)
"Waterfront cabins were amazing. The location and wildlife were serene, fantastic place to stay."
United States
Carmino
$172 nightly
The price is $192
Oct 19 - Oct 20
Total with taxes and fees
Mandala Springs Wellness Retreat Center
A white building with a black balcony, surrounded by lush greenery and trees.

5. Sebastopol Lux Walk toTown Guest Suite

Sebastopol Lux Walk toTown Guest Suite
Sebastopol
9.2 out of 10, Wonderful, (7 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
$249 nightly
The price is $266
Nov 3 - Nov 4
Total with taxes and fees
Sebastopol Lux Walk toTown Guest Suite
Private kitchen

6. 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.
$317 nightly
The price is $356
Oct 13 - Oct 14
Total with taxes and fees
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
An outdoor seating area with a table, candles, and a potted plant.

7. Comfort and Style in Our Queen Cottage

Comfort and Style in Our Queen Cottage
Calistoga
9.8 out of 10, Exceptional, (49 reviews)
"Great place to stay. Clean and well appointed and in a great location for access to sites, vineyards, and restaurants "
United States
Robert
$214 nightly
The price is $242
Nov 1 - Nov 2
Total with taxes and fees
Comfort and Style in Our Queen Cottage
A beach with a large rock formation, a sandy shore, and a calm sea.

8. The Tiny Tipsy Turtle

The Tiny Tipsy Turtle
Guerneville
10.0 out of 10, Exceptional, (66 reviews)
"Great little place to stay / perfect location in town close to everything / wonderful front patio "
United States
ANTHONY B.
$203 nightly
The price is $217
Oct 18 - Oct 19
Total with taxes and fees
The Tiny Tipsy Turtle
A spacious lobby with a large sofa, a coffee table, and a leather armchair. A fireplace is visible in the background, and there is a staircase leading to an upper level.

9. Sonoma Stonehouse, Wine Country Vibes

Sonoma Stonehouse, Wine Country Vibes
2.0 star property
Santa Rosa
9.0 out of 10, Wonderful, (2 reviews)
"What a lovely place to stay! Seamless check in and check out. Host answered every question quickly. Other rooms/guests were never heard entering or exiting. Clean and comfy."
United States
Tresa
$455 nightly
The price is $528
Oct 23 - Oct 24
Total with taxes and fees
Sonoma Stonehouse, Wine Country Vibes
A spacious kitchen with a large island, wooden ceiling, and large windows offering a view of the deck.

10. 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.
$376 nightly
The price is $416
Oct 25 - Oct 26
Total with taxes and fees
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
A covered outdoor deck with a table and chairs, a grill, and a bottle of wine.

11. Cobb Mountain Chalet King Size Suite

Cobb Mountain Chalet King Size Suite
Cobb
9.2 out of 10, Wonderful, (30 reviews)
"My husband and I cannot stop talking about this beautiful, serene gem. Each room was immaculate. The sofas were so cozy and plenty of soft blankets! The market is equipped with everything & just a few minutes away. We are house hunting & can’t wait to return to the chalet!"
United States
Roberta F.
$159 nightly
The price is $175
Oct 14 - Oct 15
Total with taxes and fees
Cobb Mountain Chalet King Size Suite
An outdoor patio with wooden chairs and a table, surrounded by greenery and a white pergola.

12. 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
$339 nightly
The price is $375
Nov 9 - Nov 10
Total with taxes and fees
Peaceful, charming, cottage in wine country. Beautiful yard!
A spacious living room with a fireplace, wooden flooring, and a cozy seating area.

13. Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA
Santa Rosa
9.8 out of 10, Exceptional, (81 reviews)
"Lovely vacation rental"
United States
suzanne g.
$434 nightly
The price is $462
Nov 2 - Nov 3
Total with taxes and fees
Wine Country Cottage in downtown Santa Rosa, CA
A coastal landscape with a beach, rocky cliffs, and colorful vegetation.

14. Historic Ranch House on a Premier Wine Label's Vineyard in Sonoma Wine Country

Historic Ranch House on a Premier Wine Label's Vineyard in Sonoma Wine Country
Sebastopol
9.8 out of 10, Exceptional, (72 reviews)
"Very beautiful property and location!"
United States
James T.
$451 nightly
The price is $499
Oct 21 - Oct 22
Total with taxes and fees
Historic Ranch House on a Premier Wine Label's Vineyard in Sonoma Wine Country
A house with a swimming pool surrounded by lush greenery and a small waterfall feature.

15. Cozy Wine Country Guesthouse with Private Pool & Yard

Cozy Wine Country Guesthouse with Private Pool & Yard
Santa Rosa
10.0 out of 10, Exceptional, (34 reviews)
"Wonderful stay!"
United States
Adam C.
$358 nightly
The price is $358
Oct 14 - Oct 15
Total with taxes and fees
Cozy Wine Country Guesthouse with Private Pool & Yard
An entrance with a wooden door, a wicker chair, a cushioned bench, a window with a view of trees, and a hanging light fixture.

16. Private Lofted Downtown Studio

Private Lofted Downtown Studio
Sebastopol
9.8 out of 10, Exceptional, (53 reviews)
"Very cute and luxurious!! We really enjoyed our stay and great proximity to downtown. "
United States
Yvonne L.
$439 nightly
The price is $485
Oct 18 - Oct 19
Total with taxes and fees
Private Lofted Downtown Studio
A hot tub with a fire feature, surrounded by a wooden deck and a covered patio area.

17. Charming Dog-Friendly Home Near Regional Park

Charming Dog-Friendly Home Near Regional Park
Sebastopol
10.0 out of 10, Exceptional, (33 reviews)
"Great place to stay"
United States
Michelle D.
$351 nightly
The price is $387
Oct 12 - Oct 13
Total with taxes and fees
Charming Dog-Friendly Home Near Regional Park
A hallway with white paneling and wooden doors, leading to an outdoor area with greenery.

18. 2BR Bungalow - Russian River & Wine Country

2BR Bungalow - Russian River & Wine Country
Forestville
9.8 out of 10, Exceptional, (20 reviews)
"Nice clean relaxing place to stay near the river! Was perfect for our little weekend getaway."
United States
Greg K.
$388 nightly
The price is $436
Oct 12 - Oct 13
Total with taxes and fees
2BR Bungalow - Russian River & Wine Country
An open doorway leading to a patio with two wicker chairs and a small table, surrounded by potted plants and a view of a green building and trees.

19. Walk to Downtown Sebastopol * Luxe Vacation Studio

Walk to Downtown Sebastopol * Luxe Vacation Studio
Sebastopol
8.4 out of 10, Very good, (7 reviews)
"This is a cute property nestled at the top of the drive in a wooded neighborhood. The outdoor niche would be a pleasant spot for reading. It has a cozy roominess with tidy appointments. It's an easy drive to the Sebastopol business district, which has a wonderful, rustic quirkiness. We highly recommend a drive to Goat Rock on the coast, then to Armstrong Redwood Reserve, and lunch at Baked on the River in Guerneville."
United States
Steven M.
$323 nightly
The price is $345
Nov 3 - Nov 4
Total with taxes and fees
Walk to Downtown Sebastopol * Luxe Vacation Studio
A deck with outdoor seating, a grill, and a view of a house with large windows.

20. Somms Rest ⎮ Designed. Curated. Peaceful.

Somms Rest ⎮ Designed. Curated. Peaceful.
Mirabel Heights
9.8 out of 10, Exceptional, (37 reviews)
"Great stay, highly recommend!"
United States
Jana P.
$465 nightly
The price is $514
Oct 14 - Oct 15
Total with taxes and fees
Somms Rest ⎮ Designed. Curated. Peaceful.
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

Oxford Suites Sonoma County

Oxford Suites Sonoma County

10/10 Excellent
"It’s always a pleasure to stay the night at the Oxford. Staff is friendly, room is spacious and clean and the bed is comfortable."
Alejandro 1-night trip
Posted 10 hours ago
Oxford Suites Sonoma County

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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