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

Chalk Hill Vacation 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
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Chalk Hill vacation 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)
"Great location!"
United States
Riley F.
The price is ￥30,493
￥68,821 total
includes taxes & fees
Jul 6 - Jul 7
Private Vineyard Retreat • Wine Tasting Perks • Fire Pit
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 ￥12,778
￥14,567 total
includes taxes & fees
Jul 6 - Jul 7
The Ranch at Lake Sonoma
Deluxe Cabin, 1 Queen Bed, Patio, Garden View | Laptop workspace, free WiFi, bed sheets

Wildhaven Sonoma Glamping

Wildhaven Sonoma Glamping
1.0 star property
Healdsburg
9.2 out of 10, Wonderful, (117 reviews)
"Nice location to go and have a good time in the family "
United States
Ismelda Cortez
The price is ￥18,406
￥20,983 total
includes taxes & fees
Aug 5 - Aug 6
Wildhaven Sonoma Glamping
Exterior

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

Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
Calistoga
9.8 out of 10, Exceptional, (41 reviews)
"Host, amenities, location….all excellent. "
United States
Amy B.
The price is ￥49,854
￥67,831 total
includes taxes & fees
Jul 6 - Jul 7
Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
Room, 1 Bedroom | Living area | Smart TV

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 ￥17,577
￥37,874 total
includes taxes & fees
Jul 8 - Jul 9
Rouge Cobb Mountain Hotel - Cabin 1
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 ￥14,359
￥31,992 total
includes taxes & fees
Jul 20 - Jul 21
Cobb Mountain Chalet King Size Suite
Smart TV

Serenity at the Russian River

Serenity at the Russian River
Mirabel Heights
10.0 out of 10, Exceptional, (39 reviews)
"Clean and comfortable place to stay, easy-check in, good amenities and location. Would definitely stay again."
United States
Scott W.
The price is ￥29,041
￥85,929 total
includes taxes & fees
Jul 6 - Jul 7
Serenity at the Russian River
Outdoor pool, a heated pool

Cozy Wine Country Guesthouse with Private Pool & Yard

Cozy Wine Country Guesthouse with Private Pool & Yard
Santa Rosa
10.0 out of 10, Exceptional, (19 reviews)
The price is ￥59,696
￥67,924 total
includes taxes & fees
Jul 27 - Jul 28
Cozy Wine Country Guesthouse with Private Pool & Yard
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 ￥28,880
￥36,761 total
includes taxes & fees
Jul 6 - Jul 7
Comfort and Style in Our Queen Cottage
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)
"Overall a good place to stay in downtown Santa Rosa. "
United States
Stan R.
The price is ￥33,075
￥68,667 total
includes taxes & fees
Aug 4 - Aug 5
Wine Country Cottage in downtown Santa Rosa, CA
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 ￥40,335
￥82,638 total
includes taxes & fees
Jul 6 - Jul 7
Glen Ellen Retreats Coastal Cottage
Meeting facility

Mandala Springs Wellness Retreat Center

Mandala Springs Wellness Retreat Center
3.5 star property
Cobb
9.0 out of 10, Wonderful, (34 reviews)
"Very clean room, friendly staff, great to walk around "
United States
Victoria
The price is ￥25,992
￥28,981 total
includes taxes & fees
Jul 8 - Jul 9
Mandala Springs Wellness Retreat Center
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, (13 reviews)
"Great stay and location!"
United States
Brandi K.
The price is ￥23,814
￥56,293 total
includes taxes & fees
Jul 7 - Jul 8
Peaceful, charming, cottage in wine country. Beautiful yard!
Property grounds

Private Lofted Downtown Studio

Private Lofted Downtown Studio
Sebastopol
9.8 out of 10, Exceptional, (48 reviews)
"Very cute and luxurious!! We really enjoyed our stay and great proximity to downtown. "
United States
Yvonne L.
The price is ￥38,480
￥79,238 total
includes taxes & fees
Jul 6 - Jul 7
Private Lofted Downtown Studio
TV, fireplace

Tranquil Redwood Retreat

Tranquil Redwood Retreat
Guerneville
8.8 out of 10, Excellent, (10 reviews)
"Perfect hun for enjoying downtown guernville "
United States
Alex A.
The price is ￥24,395
￥55,718 total
includes taxes & fees
Jul 8 - Jul 9
Tranquil Redwood Retreat
2 bedrooms, iron/ironing board, travel crib, free WiFi

Glen Ellen Retreats Sunset Cottage

Glen Ellen Retreats Sunset Cottage
Glen Ellen
10.0 out of 10, Exceptional, (79 reviews)
"Perfect for a weekend getaway with family."
United States
Tara C.
The price is ￥40,335
￥83,122 total
includes taxes & fees
Jul 7 - Jul 8
Glen Ellen Retreats Sunset Cottage
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 ￥27,105
￥48,105 total
includes taxes & fees
Jul 8 - Jul 9
Sebastopol Lux Walk toTown Guest Suite
Beach

The Tiny Tipsy Turtle

The Tiny Tipsy Turtle
Guerneville
10.0 out of 10, Exceptional, (60 reviews)
"Really great place. Highly recommend!!!"
United States
Jennifer
The price is ￥22,426
￥40,283 total
includes taxes & fees
Jul 7 - Jul 8
The Tiny Tipsy Turtle
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 ￥32,268
￥81,315 total
includes taxes & fees
Jul 7 - Jul 8
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
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, (23 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 ￥16,941
￥41,303 total
includes taxes & fees
Jul 19 - Jul 20
2 Hidden Wine Country Gem Upstairs Unit
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

Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton

Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton

10/10 Excellent
"The resort was amazing. We enjoyed the pool, restaurant and fitness classes."
Rose 2-night trip
Posted 6 hours ago
Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton

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