Chalk Hill Holiday Houses

A group of large hot air balloons, including a yellow one with a face, and a white van with cartoon characters.

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Our top choices for Chalk Hill holiday homes

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.

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

2. 2 Hidden Wine Country Gem Upstairs Unit

Scenic Brush Creek

Glen M.

includes taxes & fees

26 Oct - 27 Oct

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

Northwest Santa Rosa

kevin c.

includes taxes & fees

1 Nov - 2 Nov

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

4. Forestville Redwood Escape

Forestville

includes taxes & fees

3 Nov - 4 Nov

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

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

Sebastopol

Mikaela

includes taxes & fees

9 Nov - 10 Nov

A dining area with a wooden table and chairs, a white macrame runner, and a hanging plant.

6. Wine Country Cottage Escape

Fulton

Tina A.

includes taxes & fees

19 Oct - 20 Oct

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

7. Cobb Mountain Chalet King Size Suite

Cobb

Brigid

includes taxes & fees

19 Oct - 20 Oct

A spacious living area with a leather sofa, wooden coffee table, and a dining table with chairs. There are plants, bookshelves, and a kitchen in the background.

8. Craftsman 2 blocks from Russian River Brewery!

Santa Rosa

Thomas L.

includes taxes & fees

26 Oct - 27 Oct

A spacious kitchen with a large island, wooden ceiling, and large windows offering a view of the deck.

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

Forestville

Rebecca I.

includes taxes & fees

17 Nov - 18 Nov

A covered porch with two grey upholstered chairs and a small table, wooden railings, and a window with a curtain.

10. Tangerine Cottage spacious home

Middletown

includes taxes & fees

27 Oct - 28 Oct

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

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

Sebastopol

Rosio G.

includes taxes & fees

21 Oct - 22 Oct

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

12. Modern Country Home | Near Downtown & Bike Trail

Sebastopol

Santo Q.

includes taxes & fees

18 Oct - 19 Oct

An outdoor patio area with stone flooring, wooden tables, and wicker chairs, surrounded by lush greenery and string lights.

13. Walk to Downtown & Russian River Brewery

Santa Rosa

roxanne K.

includes taxes & fees

2 Nov - 3 Nov

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

14. Private Lofted Downtown Studio

Sebastopol

Yvonne L.

includes taxes & fees

19 Oct - 20 Oct

A deck with outdoor seating, a grill, and a view of a house with large windows.

15. Somms Rest ⎮ Designed. Curated. Peaceful.

Mirabel Heights

Jana P.

includes taxes & fees

1 Nov - 2 Nov

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.

16. 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.

includes taxes & fees

17 Nov - 18 Nov

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

17. Cozy Wine Country Guesthouse with Private Pool & Yard

Santa Rosa

Adam C.

includes taxes & fees

20 Oct - 21 Oct

A modern living room with a blue sectional sofa, a wooden coffee table, and a staircase leading to another room.

18. Serenity at the Russian River

Mirabel Heights

Patricia A.

includes taxes & fees

18 Oct - 19 Oct

A spacious living area with a wooden ceiling, a sofa, a coffee table, and a kitchen in the background.

19. Walk to Downtown Sebastopol * Luxe Vacation Living

Sebastopol

Courtney E.

includes taxes & fees

17 Nov - 18 Nov

A spacious living area with a large window, wooden ceiling beams, and a cozy seating arrangement.

20. ❤The Elegant: A Chic Healdsburg Winery Cottage! Hot Tub, Views! !❤

Healdsburg

sharon p.

includes taxes & fees

21 Oct - 22 Oct

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Top Chalk Hill Hotel Reviews

Hotel La Rose

10/10 Excellent

"What a joy to discover this place. Looking forward to visiting again."

Dry Creek Inn MOD Collection by Sonesta

8/10 Good

"The temps were in the high 90's on the day I arrived. I got into my room at 7pm and the a/c was off and the room was a literal hotbox. It was extremely uncomfortable. I had to turn on the a/c and leave for a couple hours before considering going back. Upon returning it was only a little bit better and I was uncomfortable all night. I understand that a/c units are not just 'on' in every room, that would be beyond wasteful. But when someone is coming to your hotel when you know the windows are closed and the a/c unit is off, perhaps give them a room previously occupied the night before (at the very least), or have a staff member turn the a/c on when a guest is confirmed and expected. Besides that, everything was great. Quiet, clean, location, parking. Thank you"

Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton

10/10 Excellent

"The flamingo hotel was a very pleasant surprise! If you’re a lover of that time. Or madman, you’ll absolutely love this hotel! Very thoughtful execution of the interior from the moment you drive up to all of the details in our room and bathroom. We were celebrating my husband‘s 60th birthday and our 31st wedding anniversary and the staff left a special surprise and handwritten note that was a lovely welcome to our trip and our stay. We look forward to coming back again on another trip and being able to take advantage of the beautiful pool!"

Find out more about Chalk Hill

Chalk Hill Holiday Homes information

Number of reviews	350
Accommodation	978 Holiday Homes
Lowest Price	NZ$310
Highest Price	NZ$961

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chalk Hill holiday homes

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

2. 2 Hidden Wine Country Gem Upstairs Unit