Chalk Hill Holiday Rentals: Short-Term Accommodations for Rent

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Our top choices for Chalk Hill holiday rentals

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

1. Wildhaven Sonoma Glamping

Healdsburg

NEERJA

HK$842 total

includes taxes & fees

5 Nov - 6 Nov

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

Geyserville

Evelyn

HK$708 total

includes taxes & fees

7 Oct - 8 Oct

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

3. 2 Hidden Wine Country Gem Upstairs Unit

Scenic Brush Creek

Glen M.

HK$2,204 total

includes taxes & fees

12 Oct - 13 Oct

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

4. Sebastopol Lux Walk toTown Guest Suite

Sebastopol

Brad

HK$1,900 total

includes taxes & fees

3 Nov - 4 Nov

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

5. Mandala Springs Wellness Retreat Center

Cobb

Carmino

HK$1,410 total

includes taxes & fees

11 Oct - 12 Oct

6. Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

Northwest Santa Rosa

kevin c.

HK$2,894 total

includes taxes & fees

4 Nov - 5 Nov

An outdoor seating area with a table, candles, and a potted plant.

7. Comfort and Style in Our Queen Cottage

Calistoga

Robert

HK$1,894 total

includes taxes & fees

1 Nov - 2 Nov

An outdoor patio with wooden chairs and a table, surrounded by greenery and a white pergola.

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

Sebastopol

Mikaela

HK$2,699 total

includes taxes & fees

8 Oct - 9 Oct

A bedroom with a bed, pillows, a blanket, and a painting on the wall.

9. Forestville Redwood Escape

Forestville

HK$3,265 total

includes taxes & fees

2 Nov - 3 Nov

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

Forestville

Rebecca I.

HK$3,230 total

includes taxes & fees

2 Nov - 3 Nov

A covered outdoor deck with a table and chairs, a grill, and a bottle of wine.

11. Cobb Mountain Chalet King Size Suite

Cobb

Roberta F.

HK$1,376 total

includes taxes & fees

14 Oct - 15 Oct

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

12. Wine Country Cottage in downtown Santa Rosa, CA

Santa Rosa

suzanne g.

HK$3,156 total

includes taxes & fees

7 Oct - 8 Oct

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.

13. Sonoma Stonehouse, Wine Country Vibes

Santa Rosa

Tresa

HK$4,288 total

includes taxes & fees

23 Oct - 24 Oct

A beach with a large rock formation, a sandy shore, and a calm sea.

14. The Tiny Tipsy Turtle

Guerneville

ANTHONY B.

HK$2,030 total

includes taxes & fees

18 Oct - 19 Oct

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

15. Cozy Wine Country Guesthouse with Private Pool & Yard

Santa Rosa

Adam C.

HK$2,809 total

includes taxes & fees

14 Oct - 15 Oct

A coastal landscape with a beach, rocky cliffs, and colorful vegetation.

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

Sebastopol

James T.

HK$3,912 total

includes taxes & fees

21 Oct - 22 Oct

A hallway with white paneling and wooden doors, leading to an outdoor area with greenery.

17. 2BR Bungalow - Russian River & Wine Country

Forestville

Greg K.

HK$3,421 total

includes taxes & fees

7 Oct - 8 Oct

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

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

Calistoga

Amy B.

HK$3,651 total

includes taxes & fees

7 Oct - 8 Oct

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

Sebastopol

"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."

Steven M.

HK$2,514 total

includes taxes & fees

3 Nov - 4 Nov

A modern building with a metal exterior, a wooden door, and a small window on the side.

20. Country Carriage House in Downtown Geyserville, Vineyard Views

Geyserville

Gina I.

HK$3,088 total

includes taxes & fees

5 Nov - 6 Nov

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Top Chalk Hill Hotel Reviews

Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton

10/10 Excellent

"Very relaxing. A great place to go to get away."

Calistoga Motor Lodge and Spa

10/10 Excellent

"Beautiful property—low key chic and very hospitable. Perhaps the most comfortable bed and pillows we’ve ever slept on!! Room was large and well appointed, with lovely design details and thoughtful amenities (such as multiple design-driven power outlets placed throughout the room). Staff was lovely, restaurant was really good. Have stayed in many properties in this area, and would definitely bump this to the top of our recommendations list! For travellers’ context, would compare to The Hotel San Jose in Austin or The Clayton in Denver."

DoubleTree by Hilton Sonoma - Wine Country

8/10 Good

"There seems to a plumbing issue going on with the property. Granted that it's 3 stories but the drainage does not seem to work very well when the shower is running and toilet is very slow flushing. The water pipes rattled a bit as well when turned on. AC unit was ok, not great. The bed was comfortable and the room itself was very quiet."

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Russian River Valley Holiday Rentals

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Check prices for these dates

Our top choices for Chalk Hill holiday rentals

1. Wildhaven Sonoma Glamping

2. The Ranch at Lake Sonoma

3. 2 Hidden Wine Country Gem Upstairs Unit

4. Sebastopol Lux Walk toTown Guest Suite

5. Mandala Springs Wellness Retreat Center

6. Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

7. Comfort and Style in Our Queen Cottage

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

9. Forestville Redwood Escape

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

11. Cobb Mountain Chalet King Size Suite

12. Wine Country Cottage in downtown Santa Rosa, CA

13. Sonoma Stonehouse, Wine Country Vibes

14. The Tiny Tipsy Turtle

15. Cozy Wine Country Guesthouse with Private Pool & Yard

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

17. 2BR Bungalow - Russian River & Wine Country

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

19. Walk to Downtown Sebastopol * Luxe Vacation Studio

20. Country Carriage House in Downtown Geyserville, Vineyard Views

Find holiday rentals that suit your style

Top Chalk Hill Hotel Reviews

Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton

Hyatt Regency Sonoma Wine Country

The Inn at the Tides

Oxford Suites Sonoma County

Calistoga Motor Lodge and Spa

DoubleTree by Hilton Sonoma - Wine Country

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

Find out more about Chalk Hill

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