Chalk Hill Vacation Rentals

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Our top choices for Chalk Hill vacation rentals

Peaceful Healdsburg Wine Country Retreat with Vineyard Views

Peaceful Healdsburg Wine Country Retreat with Vineyard Views
Healdsburg
10.0 out of 10, Exceptional, (10 reviews)
"Kitchen was great, easy area for our dog.."
United States
Brad G.
$349 nightly
The price is $386
Apr 27 - Apr 28
Total with taxes and fees
Peaceful Healdsburg Wine Country Retreat with Vineyard Views

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
$209 nightly
The price is $233
Apr 17 - Apr 18
Total with taxes and fees
Backyard Garden Oasis

Sonoma Stonehouse, Wine Country Vibes

Sonoma Stonehouse, Wine Country Vibes
2.0 star property
Santa Rosa
8.0 out of 10, Very Good, (1 review)
"Muy bonito diseño interior en ambos la recepción y el cuarto."
Mexico
Tara
$243 nightly
The price is $282
Apr 12 - Apr 13
Total with taxes and fees
Sonoma Stonehouse, Wine Country Vibes

Rouge Cobb Mountain Hotel - Cabin 1

Rouge Cobb Mountain Hotel - Cabin 1
2.0 star property
Cobb
$214 nightly
The price is $238
Apr 12 - Apr 13
Total with taxes and fees
Rouge Cobb Mountain Hotel - Cabin 1

2BR Bungalow | Russian River & Wine Country

2BR Bungalow | Russian River & Wine Country
Forestville
10.0 out of 10, Exceptional, (7 reviews)
"The place was beautiful! We had everything we needed for a great stay!"
United States
Jenn L.
$359 nightly
The price is $403
Apr 13 - Apr 14
Total with taxes and fees
2BR Bungalow | Russian River & Wine Country

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

Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
Calistoga
9.6 out of 10, Exceptional, (35 reviews)
"Perfect little cottage within walking distance to everything in downtown Calistoga! Bed was so comfy and the fireplace made it feel extra cozy. We definitely want to stay here again!"
United States
Cameron D.
$318 nightly
The price is $382
Apr 13 - Apr 14
Total with taxes and fees
Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown

Glen Ellen Retreats Coastal Cottage

Glen Ellen Retreats Coastal Cottage
Glen Ellen
10.0 out of 10, Exceptional, (162 reviews)
"Absolutely loved our time at the Glen Ellen retreat. The home is so cozy and welcoming. "
United States
Amanda D.
$471 nightly
The price is $523
Apr 12 - Apr 13
Total with taxes and fees
Glen Ellen Retreats Coastal Cottage

Glen Ellen Retreats Sunset Cottage

Glen Ellen Retreats Sunset Cottage
Glen Ellen
10.0 out of 10, Exceptional, (75 reviews)
"Perfect for a weekend getaway with family."
United States
Tara C.
$475 nightly
The price is $527
Apr 13 - Apr 14
Total with taxes and fees
Glen Ellen Retreats Sunset Cottage

Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed

Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed
Calistoga
10.0 out of 10, Exceptional, (3 reviews)
"Loved everything Ellen was very accommodating ,pleasant and polite As well as professional The furnishings were very up scale and same style as my home One suggestion The tv should be more accessible so it does not block AC when pulled out from the wall I’m not being critical because I love this place. I will stay there every time I would ever be close to Calistoga. AND I adore Ellen personally and professionally!!👍❤️"
United States
Ronny
$318 nightly
The price is $382
Apr 13 - Apr 14
Total with taxes and fees
Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed

Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK

Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Guerneville
10.0 out of 10, Exceptional, (1 review)
"Our stay was fantastic! The cabin was everything we needed for a few days; cozy, and quiet. The outdoor spaces were great and the hot tub was perfect at the end of the day. The host was super helpful and responded to my questions almost immediately. "
United States
Rosa N.
$386 nightly
The price is $434
Apr 14 - Apr 15
Total with taxes and fees
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK

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.
$241 nightly
The price is $271
Apr 15 - Apr 16
Total with taxes and fees
2 Hidden Wine Country Gem Upstairs Unit

Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA
Santa Rosa
9.6 out of 10, Exceptional, (72 reviews)
"Good location for coffee and restaurant. Nice backyard "
United States
vicki a.
$384 nightly
The price is $407
Apr 22 - Apr 23
Total with taxes and fees
Wine Country Cottage in downtown Santa Rosa, CA

Glen Ellen Retreats Hot Tub Cottage

Glen Ellen Retreats Hot Tub Cottage
Glen Ellen
10.0 out of 10, Exceptional, (85 reviews)
"Great house in a perfect location. Short distance to Jack London State Park, various wineries, and walking distance to lovely restaurants near by. We enjoyed our long weekend and will definitely stay here again when we're up in the area!"
United States
sandra h.
$512 nightly
The price is $567
Apr 12 - Apr 13
Total with taxes and fees
Glen Ellen Retreats Hot Tub Cottage

Sebastopol Lux Walk toTown Guest Suite

Sebastopol Lux Walk toTown Guest Suite
Sebastopol
9.4 out of 10, Exceptional, (3 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.
$242 nightly
The price is $258
Apr 13 - Apr 14
Total with taxes and fees
Sebastopol Lux Walk toTown Guest Suite

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

The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
Forestville
9.8 out of 10, Exceptional, (9 reviews)
"The house is beautiful and has everything you need to have a great time in forestville!"
United States
Nick C.
$450 nightly
The price is $498
Apr 12 - Apr 13
Total with taxes and fees
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville

Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries

Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
Northwest Santa Rosa
9.8 out of 10, Exceptional, (73 reviews)
"Loved our stay!!"
United States
kristen s.
$460 nightly
The price is $516
Apr 14 - Apr 15
Total with taxes and fees
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries

The Sonoma Spyglass | Incredible Views + Sauna

The Sonoma Spyglass | Incredible Views + Sauna
Sebastopol
10.0 out of 10, Exceptional, (5 reviews)
"Very clean with scenic view and well maintained. The owners did a great job with the decor and architecture. Will definitely stay again and recommend!"
United States
Victor B.
$688 nightly
The price is $760
Apr 13 - Apr 14
Total with taxes and fees
The Sonoma Spyglass | Incredible Views + Sauna

Cobb Mountain Chalet King Size Suite

Cobb Mountain Chalet King Size Suite
Cobb
9.2 out of 10, Wonderful, (25 reviews)
"Wonderful spot! Clean, quiet, great, shower and lovely deck. "
United States
Chloe K.
$143 nightly
The price is $157
Apr 20 - Apr 21
Total with taxes and fees
Cobb Mountain Chalet King Size Suite

Spacious 3BR 2BA Villa with Bocce Court near Matanzas Creek Winery

Spacious 3BR 2BA Villa with Bocce Court near Matanzas Creek Winery
Santa Rosa
9.4 out of 10, Exceptional, (25 reviews)
"Excellent place to relax with my family!"
United States
Tatem D.
$483 nightly
The price is $534
Apr 13 - Apr 14
Total with taxes and fees
Spacious 3BR 2BA Villa with Bocce Court near Matanzas Creek Winery

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
$204 nightly
The price is $231
Apr 12 - Apr 13
Total with taxes and fees
Comfort and Style in Our Queen 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.
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Top Chalk Hill Hotel Reviews

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.