Chalk Hill Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Chalk Hill holiday rentals

Terrace/patio

Private Vineyard Retreat • Wine Tasting Perks • Fire Pit

Private Vineyard Retreat • Wine Tasting Perks • Fire Pit
Healdsburg
10.0 out of 10, Exceptional, (14 reviews)
"This is a great property! Everything about it from the beginning to the end was amazing. Our two fur babies agree as well. Glenn is a great host, always available if needed. Definitely would stay again. "
United States
Audie P.
The price is HK$1,270
HK$3,082 total
includes taxes & fees
30 Jun - 1 Jul
Private Vineyard Retreat • Wine Tasting Perks • Fire Pit
Laptop workspace, free WiFi, bed sheets

Wildhaven Sonoma Glamping

Wildhaven Sonoma Glamping
1.0 star property
Healdsburg
9.2 out of 10, Wonderful, (112 reviews)
"Nice location to go and have a good time in the family "
United States
Ismelda Cortez
The price is HK$1,103
HK$1,258 total
includes taxes & fees
25 Jun - 26 Jun
Wildhaven Sonoma Glamping
Exterior

The Ranch at Lake Sonoma

The Ranch at Lake Sonoma
1.0 star property
Geyserville
9.6 out of 10, Exceptional, (4 reviews)
"Nice camping spot "
United States
Evelyn
The price is HK$621
HK$708 total
includes taxes & fees
24 Jun - 25 Jun
The Ranch at Lake Sonoma
Interior

Creekside Under the Redwoods

Creekside Under the Redwoods
Guerneville
9.8 out of 10, Exceptional, (20 reviews)
"Very cute and comfortable place! We enjoyed our stay!"
United States
Kathy M.
The price is HK$1,185
HK$2,730 total
includes taxes & fees
24 Jun - 25 Jun
Creekside Under the Redwoods
Living area

Rouge Cobb Mountain Hotel - Cabin 1

Rouge Cobb Mountain Hotel - Cabin 1
2.0 star property
Cobb
10.0 out of 10, Exceptional, (1 review)
"Quaint mountain cabin, relaxing, clean, pet friendly, easy check in"
United States
Bethany
The price is HK$999
HK$2,048 total
includes taxes & fees
24 Jun - 25 Jun
Rouge Cobb Mountain Hotel - Cabin 1
Porch

Backyard Garden Oasis

Backyard Garden Oasis
3.0 star property
Middletown
9.6 out of 10, Exceptional, (51 reviews)
"Cute garden area, quiet, nice all inclusive spot"
United States
Jodi
The price is HK$1,638
HK$1,826 total
includes taxes & fees
3 Jul - 4 Jul
Backyard Garden Oasis
Outdoor dining

Cobb Mountain Chalet King Size Suite

Cobb Mountain Chalet King Size Suite
Cobb
9.4 out of 10, Exceptional, (28 reviews)
"The property is very clean and quiet. A lovely place to stay! "
United States
MIKE
The price is HK$501
HK$1,327 total
includes taxes & fees
30 Jun - 1 Jul
Cobb Mountain Chalet King Size Suite
Outdoor dining

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

Peaceful, charming, cottage in wine country. Beautiful yard!
Sebastopol
10.0 out of 10, Exceptional, (12 reviews)
"Great stay and location!"
United States
Brandi K.
The price is HK$1,100
HK$2,585 total
includes taxes & fees
24 Jun - 25 Jun
Peaceful, charming, cottage in wine country. Beautiful yard!
Exterior

Sebastopol Lux Walk toTown Guest Suite

Sebastopol Lux Walk toTown Guest Suite
Sebastopol
8.6 out of 10, Excellent, (4 reviews)
"This is a wonderful place to stay in Sebastopol. It is comfortable, cosy, quiet and well appointed - comparable to a suite in a nice hotel. There is good access, parking and a great location. Everything worked perfectly. The only issue is that entry to the room is via a spiral stair case that would be difficult for some people with disabilities. "
United States
Joe B.
The price is HK$1,234
HK$2,135 total
includes taxes & fees
24 Jun - 25 Jun
Sebastopol Lux Walk toTown Guest Suite
Interior

2BR Bungalow | Russian River & Wine Country

2BR Bungalow | Russian River & Wine Country
Forestville
10.0 out of 10, Exceptional, (15 reviews)
"Lovely spot for a weekend in Russian River"
United States
Emily F.
The price is HK$1,187
HK$3,432 total
includes taxes & fees
24 Jun - 25 Jun
2BR Bungalow | Russian River & Wine Country
Terrace/patio

Glen Ellen Retreats Coastal Cottage

Glen Ellen Retreats Coastal Cottage
Glen Ellen
10.0 out of 10, Exceptional, (166 reviews)
"Fantastic getaway location. What a lovely town Glen Ellen is and convenient walking distance to coffee, shops and food as well as any sundries you may need. Highly recommend it as a great getaway great getaway."
United States
Randall
The price is HK$1,960
HK$4,039 total
includes taxes & fees
24 Jun - 25 Jun
Glen Ellen Retreats Coastal Cottage
Outdoor pool

2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (22 reviews)
"We enjoyed our stay and would certainly use this rental again if we're ever in the area. "
United States
Glen M.
The price is HK$876
HK$2,082 total
includes taxes & fees
6 Jul - 7 Jul
2 Hidden Wine Country Gem Upstairs Unit
Property grounds

Private Lofted Downtown Studio

Private Lofted Downtown Studio
Sebastopol
9.8 out of 10, Exceptional, (48 reviews)
"Fabulous, beautiful and within walking distance to downtown!"
United States
Jacqui S.
The price is HK$1,869
HK$3,825 total
includes taxes & fees
24 Jun - 25 Jun
Private Lofted Downtown Studio
TV

Emerald Lodge quiet efficiency

Emerald Lodge quiet efficiency
Middletown
10.0 out of 10, Exceptional, (3 reviews)
"Very homey comfortable place. Peaceful 😊"
United States
Carol
The price is HK$901
HK$1,724 total
includes taxes & fees
9 Jul - 10 Jul
Emerald Lodge quiet efficiency
2 bedrooms, desk, iron/ironing board, free WiFi

Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA
Santa Rosa
9.8 out of 10, Exceptional, (77 reviews)
"Had everything we needed! "
United States
Kristen Y.
The price is HK$1,528
HK$3,271 total
includes taxes & fees
28 Jun - 29 Jun
Wine Country Cottage in downtown Santa Rosa, CA
Fridge, microwave, oven, stovetop

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.
The price is HK$1,489
HK$3,669 total
includes taxes & fees
24 Jun - 25 Jun
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Dining

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
The price is HK$1,403
HK$1,770 total
includes taxes & fees
24 Jun - 25 Jun
Comfort and Style in Our Queen Cottage
Dining

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, (11 reviews)
"The house is beautiful and has everything you need to have a great time in forestville!"
United States
Nick C.
The price is HK$1,567
HK$3,958 total
includes taxes & fees
25 Jun - 26 Jun
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
Dining

Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is HK$1,293
HK$2,912 total
includes taxes & fees
25 Jun - 26 Jun
Wine Country Cottage Escape
Terrace/patio

Glen Ellen Retreats Hot Tub Cottage

Glen Ellen Retreats Hot Tub Cottage
Glen Ellen
10.0 out of 10, Exceptional, (90 reviews)
"Beautiful home and very quiet town. Enjoyed my stay! "
United States
Adrian P.
The price is HK$2,266
HK$4,444 total
includes taxes & fees
7 Jul - 8 Jul
Glen Ellen Retreats Hot Tub Cottage
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chalk Hill Hotel Reviews

Solage, Auberge Collection

Solage, Auberge Collection

10/10 Excellent
"Amazing and peaceful"
Lisa 2-night trip
Posted 1 hour ago
Solage, Auberge Collection

Find out more about Chalk Hill

Search for holiday rentals in Chalk Hill on Expedia! You can easily find your home rentals, villas, holiday apartments in Chalk Hill using one of the methods below:

  • View our selection of featured holiday rentals in Chalk Hill
  • Use the map to find apartments and other holiday homes in the Chalk Hill neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chalk Hill while they last

Look no further and take a look at our great range of rental properties in Chalk Hill!

Explore a world of travel with Expedia