Chalk Hill Vacation Rentals from $90: Search Short-Term Rentals

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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

Healdsburg

Mark R.

$387 nightly

Oct 29 - Oct 30

Total with taxes and fees

A wooden sauna structure with a bench inside, a small pool, and a potted plant outside.

2. Sauna, Cold Plunge & Fire Pit Near Wineries

Windsor

Keri S.

$924 nightly

Oct 26 - Oct 27

Total with taxes and fees

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

3. Wildhaven Sonoma Glamping

Healdsburg

NEERJA

$104 nightly

Nov 19 - Nov 20

Total with taxes and fees

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.

4. Sonoma Stonehouse, Wine Country Vibes

Santa Rosa

Tresa

$383 nightly

Oct 23 - Oct 24

Total with taxes and fees

A room with a brown sofa, two wicker chairs, a small table with a lamp, and a framed picture on the wall.

5. Hideaway Cottages

Calistoga

$218 nightly

Oct 21 - Oct 22

Total with taxes and fees

A white building with a covered porch, potted plants, and a bicycle.

6. Mandala Springs Wellness Retreat Center

Cobb

Carmino

$154 nightly

Oct 21 - Oct 22

Total with taxes and fees

A single-story cabin with a small porch, situated on a hillside overlooking a body of water and mountains.

7. The Ranch at Lake Sonoma

Geyserville

Evelyn

$79 nightly

Oct 21 - Oct 22

Total with taxes and fees

A house with a swimming pool surrounded by lush greenery and a small waterfall feature.

8. Cozy Wine Country Guesthouse with Private Pool & Yard

Santa Rosa

Adam C.

$358 nightly

Oct 21 - Oct 22

Total with taxes and fees

A spacious living room with a fireplace, wooden flooring, and a cozy seating area.

9. Wine Country Cottage in downtown Santa Rosa, CA

Santa Rosa

suzanne g.

$432 nightly

Oct 26 - Oct 27

Total with taxes and fees

A swimming pool with a slide, a barbecue area, and a wooden deck.

10. 2 Hidden Wine Country Gem Upstairs Unit

Scenic Brush Creek

Glen M.

$248 nightly

Oct 25 - Oct 26

Total with taxes and fees

A small, single-story house with a front porch, a chimney, and a door with a window above it.

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

Calistoga

"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...

William

$397 nightly

Oct 21 - Oct 22

Total with taxes and fees

An entrance with a wooden door, a wicker chair, a cushioned bench, a window with a view of trees, and a hanging light fixture.

12. Private Lofted Downtown Studio

Sebastopol

Yvonne L.

$436 nightly

Oct 27 - Oct 28

Total with taxes and fees

A house with a porch, a wooden door, and two rocking chairs. There are two suitcases and a table with bottles on the porch.

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

Calistoga

"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!"

Jennifer G.

$397 nightly

Oct 21 - Oct 22

Total with taxes and fees

A modern kitchen with white cabinets, a central island, and a dining area with a round table and chairs.

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

Northwest Santa Rosa

Melissa M.

$489 nightly

Oct 21 - Oct 22

Total with taxes and fees

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

Calistoga

Paul L.

$399 nightly

Oct 21 - Oct 22

Total with taxes and fees

An outdoor patio with a wooden deck, a table with chairs, and a door with a hanging light fixture.

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

Santa Rosa

Abigail M.

$435 nightly

Oct 21 - Oct 22

Total with taxes and fees

A living room with a wooden dining table set for four, a black sofa, and a small coffee table.

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

Santa Rosa

Howard

$536 nightly

Oct 25 - Oct 26

Total with taxes and fees

A white building with a black balcony, surrounded by lush greenery and trees.

18. Sebastopol Lux Walk toTown Guest Suite

Sebastopol

Brad

$235 nightly

Nov 17 - Nov 18

Total with taxes and fees

A backyard with a hot tub, wooden pergola, and a barbecue area.

19. Wine Country Backyard Escape

Santa Rosa

suzanne s.

$1,037 nightly

Oct 31 - Nov 1

Total with taxes and fees

A modern house with a stone fireplace, a swimming pool, and outdoor furniture.

20. Sebastopol Luxury Home With Views, Pool & Hot tub

Sebastopol

Joseph B.

$1,332 nightly

Oct 24 - Oct 25

Total with taxes and fees

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Top Chalk Hill Hotel Reviews

Oxford Suites Sonoma County

10/10 Excellent

"Oxford Suites exceeded all my expectations. Loved the room and the amenities were fantastic!"

Rodeway Inn Wine Country

10/10 Excellent

"Small room with 2 Queen, even makes the room smaller. My fiancé was using a walker, makes harder for her to move around. A king bed would be good, lots of space to move around, I am talking about room 118. Your online photos didn't match the actual room now. We are booking again for this weekend. Please give us a better room. Close to the freeway and Graton."

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

8/10 Good

"Our experience was mostly very positive. The room was very clean and the bed was quite comfortable. My complaints are that the pool was too cold for an evening swim and the complimentary breakfast was not well maintained. We had to report to the desk that there were no eggs or biscuits. It took a while, and when they were brought in the biscuits were okay but the eggs were not all that great. Also, while not the hotel's fault, the street noise was quite loud in our room in the early evening. It settled down around 10:00. That said, I would stay here again."

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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Check prices for these dates

Our top choices for Chalk Hill vacation rentals

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

2. Sauna, Cold Plunge & Fire Pit Near Wineries

3. Wildhaven Sonoma Glamping

4. Sonoma Stonehouse, Wine Country Vibes

5. Hideaway Cottages

6. Mandala Springs Wellness Retreat Center

7. The Ranch at Lake Sonoma

8. Cozy Wine Country Guesthouse with Private Pool & Yard

9. Wine Country Cottage in downtown Santa Rosa, CA

10. 2 Hidden Wine Country Gem Upstairs Unit

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

12. Private Lofted Downtown Studio

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

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

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

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

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

18. Sebastopol Lux Walk toTown Guest Suite

19. Wine Country Backyard Escape

20. Sebastopol Luxury Home With Views, Pool & Hot tub

Find vacation rentals that suit your style

Top Chalk Hill Hotel Reviews

Oxford Suites Sonoma County

Find out more about Chalk Hill

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