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Chalk Hill Vacation Rentals

Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

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)
"The house was just like advertised. Great location to visit the surrounding area."
United States
David S.
$358 nightly
The price is $396
Sep 21 - Sep 22
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. 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.
$793 nightly
The price is $893
Sep 1 - Sep 2
Total with taxes and fees
Wildflower
A cozy cabin with a loft bedroom, wooden exterior, and a small balcony.

3. Wildhaven Sonoma Glamping

Wildhaven Sonoma Glamping
1.0 star property
Healdsburg
9.2 out of 10, Wonderful, (131 reviews)
"Nice place to be in with your dog, very good for comfortable stay"
United States
NEERJA
$110 nightly
The price is $125
Sep 1 - Sep 2
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.

4. The Ranch at Lake Sonoma

The Ranch at Lake Sonoma
1.0 star property
Geyserville
9.6 out of 10, Exceptional, (5 reviews)
"Nice camping spot "
United States
Evelyn
$67 nightly
The price is $77
Aug 31 - Sep 1
Total with taxes and fees
The Ranch at Lake Sonoma

5. 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.
$385 nightly
The price is $432
Sep 8 - Sep 9
Total with taxes and fees
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
A swimming pool with a slide, a barbecue area, and a wooden deck.

6. 2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (28 reviews)
"We enjoyed our stay and would certainly use this rental again if we're ever in the area. "
United States
Glen M.
$220 nightly
The price is $246
Sep 20 - Sep 21
Total with taxes and fees
2 Hidden Wine Country Gem Upstairs Unit
An outdoor patio with wooden chairs and a table, surrounded by greenery and a white pergola.

7. 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
$307 nightly
The price is $339
Sep 2 - Sep 3
Total with taxes and fees
Peaceful, charming, cottage in wine country. Beautiful yard!
An outdoor patio with a pergola labeled 'Brewing Station,' surrounded by chairs and a table, with string lights overhead.

8. Russian River Brew-cation Home

Russian River Brew-cation Home
Northwest Santa Rosa
10.0 out of 10, Exceptional, (56 reviews)
"What a perfect place to stay for a wine country weekend! We’ll definitely be back!"
United States
Gina N.
$479 nightly
The price is $538
Sep 1 - Sep 2
Total with taxes and fees
Russian River Brew-cation Home
A white building with a black balcony, surrounded by lush greenery and trees.

9. Sebastopol Lux Walk toTown Guest Suite

Sebastopol Lux Walk toTown Guest Suite
Sebastopol
9.0 out of 10, Wonderful, (6 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
$255 nightly
The price is $273
Sep 16 - Sep 17
Total with taxes and fees
Sebastopol Lux Walk toTown Guest Suite
A modern kitchen with white cabinets, a central island, and a dining area with a round table and chairs.

10. 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, (84 reviews)
"We enjoyed our stay. We had a lovely girls weekend and had no issues. The owner was very responsive and helpful."
United States
Avani S.
$479 nightly
The price is $538
Aug 31 - Sep 1
Total with taxes and fees
Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts
A spacious living room with a fireplace, wooden flooring, and a cozy seating area.

11. Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA
Santa Rosa
9.8 out of 10, Exceptional, (79 reviews)
"Lovely vacation rental"
United States
suzanne g.
$400 nightly
The price is $424
Aug 31 - Sep 1
Total with taxes and fees
Wine Country Cottage in downtown Santa Rosa, CA
A spacious kitchen with a large island, wooden ceiling, and large windows offering a view of the deck.

12. 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, (14 reviews)
"The house is beautiful and has everything you need to have a great time in forestville!"
United States
Nick C.
$400 nightly
The price is $442
Sep 1 - Sep 2
Total with taxes and fees
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
A modern living room with a blue sectional sofa, a wooden coffee table, and a staircase leading to another room.

13. 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
$488 nightly
The price is $540
Aug 31 - Sep 1
Total with taxes and fees
Serenity at the Russian River
A deck with outdoor seating, a grill, and a view of a house with large windows.

14. Somms Rest ⎮ Designed. Curated. Peaceful.

Somms Rest ⎮ Designed. Curated. Peaceful.
Mirabel Heights
9.8 out of 10, Exceptional, (36 reviews)
"Great stay, highly recommend!"
United States
Jana P.
$468 nightly
The price is $517
Sep 8 - Sep 9
Total with taxes and fees
Somms Rest ⎮ Designed. Curated. Peaceful.
A row of cabins surrounded by tall trees in a forested area.

15. 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
$188 nightly
The price is $210
Aug 31 - Sep 1
Total with taxes and fees
Rouge Cobb Mountain Hotel - Cabin 3
A shuffleboard table in a room with wooden walls and large windows.

16. Relaxing Vineyard View, Rooftop Deck & Game Room

Relaxing Vineyard View, Rooftop Deck & Game Room
Sebastopol
10.0 out of 10, Exceptional, (26 reviews)
"The location was perfect if you enjoy the Russian River Wineries and the Healdsburg area. The house itself is full of charm and character. It was nice to be able to unwind with friends at the dining table and play cards after a collaboratively cooked meal. The little town of Graton has a couple of good little restaurants, too!"
United States
Jeff D.
$451 nightly
The price is $508
Aug 31 - Sep 1
Total with taxes and fees
Relaxing Vineyard View, Rooftop Deck & Game Room
A wooden interior with a dining area, a bench, and a mirror on the wall.

17. Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.8 out of 10, Exceptional, (22 reviews)
"It was wonderful, we'll be back!"
United States
Jehanne H.
$436 nightly
The price is $490
Aug 31 - Sep 1
Total with taxes and fees
Cozy Riverfront Cabin - Beach Access & Wood Stove
A white building with a covered porch, potted plants, and a bicycle.

18. Mandala Springs Wellness Retreat Center

Mandala Springs Wellness Retreat Center
3.5 star property
Cobb
9.0 out of 10, Wonderful, (36 reviews)
"Waterfront cabins were amazing. The location and wildlife were serene, fantastic place to stay."
United States
Carmino
$176 nightly
The price is $196
Sep 8 - Sep 9
Total with taxes and fees
Mandala Springs Wellness Retreat Center
A hot tub on a wooden deck with a view of a forested area.

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

Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Guerneville
9.0 out of 10, Wonderful, (6 reviews)
"Our stay was fantastic! The cabin was everything we needed for a few days; cozy, and quiet. The outdoor spaces were great and the hot tub was perfect at the end of the day. The host was super helpful and responded to my questions almost immediately. "
United States
Rosa N.
$391 nightly
The price is $439
Sep 1 - Sep 2
Total with taxes and fees
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
A living room with a stone fireplace, wooden flooring, a dining area with chairs, and a large window.

20. 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.
$509 nightly
The price is $563
Aug 31 - Sep 1
Total with taxes and fees
Wine Country Getaway
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

Hotel La Rose

Hotel La Rose

8/10 Good
"Great communication. Very comfortable beds."
Heidi 1-night trip
Posted 11 hours ago
Hotel La Rose

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 $77 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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