Photo by Jennifer Hill

Chalk Hill Vacation Rentals

April 2025

SundayMondayTuesdayWednesdayThursdayFridaySaturday

May 2025

SundayMondayTuesdayWednesdayThursdayFridaySaturday
    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Vacation Rentals in Chalk Hill

Chalk Hill Cottage Close to Wineries

9.8 out of 10, Exceptional, (34)
"The cottage was spacious and in a great location."
Chalk Hill Cottage Close to Wineries

Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard

9.8 out of 10, Exceptional, (430)
"It’s such a treat to stay at Aftermath. My family was bowled over at the spectacular views and cozy cottage. "
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard

COZY...Dog-Friendly...BUNGALOW—Perfect for Couples!!!

9.6 out of 10, Exceptional, (168)
"Excellent location to be near bodega bay restaurants and The headlands -very nice and approachable host, very dog friendly place. "
COZY...Dog-Friendly...BUNGALOW—Perfect for Couples!!!

Romantic Redwood Hideaway - Hot Tub, Hammock, Walk to Russian River and Downtown

10.0 out of 10, Exceptional, (28)
"We enjoyed our stay here. The private hot tub was perfect after a long day. Convenient location close to great restaurants, wineries, and Armstrong woods. "
The price is CA $325
CA $631 total
includes taxes & fees
Apr 27 - Apr 28
Romantic Redwood Hideaway - Hot Tub, Hammock, Walk to Russian River and Downtown

Oceanfront - Hot Tub - Newly Remodeled Cottage

9.8 out of 10, Exceptional, (374)
"Would stay here again! House had plenty of space for the family. We enjoyed the hot tub and the great view. Can’t wait for next time."
Oceanfront - Hot Tub - Newly Remodeled Cottage

4.5 Bedrooms, 3 Baths, 2 Kitchens, 180 degree views and a 'Man Cave'

9.2 out of 10, Wonderful, (170)
"Great house with lots of amenities. Also had a pool table and a video game console. Good location with an excellent view of the sunset when not foggy. Our family had a great time and we would stay there again in the future."
4.5 Bedrooms, 3 Baths, 2 Kitchens, 180 degree views and a 'Man Cave'

Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella

10.0 out of 10, Exceptional, (61)
"This property was amazing from top to bottom and had everything you could ask for. Gym, tennis court, bocci ball court, sauna, steam, movie room oh and let’s not forget your own wine cave! We had a chef come one night and we did dinner in the cave and it was amazing! I would recommend this property to anybody, it reminded me of sitting in Tuscany with the view we had! "
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella

3 bd 2 ba Vineyard View Farmhouse close to downtown St. Helena Permit PL24-006

10.0 out of 10, Exceptional, (120)
"This is the perfect location because you are secluded yet a short walk into town"
3 bd 2 ba Vineyard View Farmhouse close to downtown St. Helena Permit PL24-006

Wine Country Getaway

10.0 out of 10, Exceptional, (20)
"great property."
The price is CA $331
CA $805 total
includes taxes & fees
Apr 23 - Apr 24
Wine Country Getaway

Wine Country Harvest Vacation Home

9.8 out of 10, Exceptional, (73)
"Very private large house and yard perfect!"
Wine Country Harvest Vacation Home

Vineyard cottage with a hot tub, fireplace, washer/dryer & vineyard views

8.4 out of 10, Very good, (23)
"This place was so ideal. Beautiful outdoor area, plenty of room for socializing as well as privacy. So great!"
Vineyard cottage with a hot tub, fireplace, washer/dryer & vineyard views

New Modern House in Sonoma Valley's Best Area

10.0 out of 10, Exceptional, (248)
"A lovely modern house in a nature filled woodland. It was a lovely stay!"
New Modern House in Sonoma Valley's Best Area

Downtown St. Helena retreat with pool, bocce ball and privacy. Permit #PL23-019

9.8 out of 10, Exceptional, (86)
"The home was located in a beautiful area. Lots of great shops and restaurants within walking distance."
Downtown St. Helena retreat with pool, bocce ball and privacy. Permit #PL23-019

Escape to Wine County in your independant Cottage in Downtown Calistoga

9.8 out of 10, Exceptional, (13)
"We have stayed many times at the Cottage Grove Inn and it never disappoints. "
The price is CA $381
CA $520 total
includes taxes & fees
Apr 23 - Apr 24
Escape to Wine County in your independant Cottage in Downtown Calistoga

Double Queen Room Non-vaulted with Ocean View!

9.0 out of 10, Wonderful, (6)
"Nice little property overlooking the water. I would stay here again."
The price is CA $183
CA $242 total
includes taxes & fees
Apr 23 - Apr 24
Double Queen Room Non-vaulted with Ocean View!

Bodega Bay on the Edge of Pacific Ocean

9.6 out of 10, Exceptional, (132)
"We had a wonderful stay. The house is super comfy and cozy and was perfect for our visit with small children. We especially enjoyed the access to the beach out of the backyard. Can't wait to come back!"
Bodega Bay on the Edge of Pacific Ocean

Updated, dog-friendly cottage with bay views, wraparound deck & EV charger

9.6 out of 10, Exceptional, (45)
"We came back to this wonderful cottage and will continue to return in the future. It is cozy and comfy, it is fully stocked, doggie supplies too, in an awesome neighborhood, close to everything in Bodega Bay. Check in and out is so easy. And the communication with property management is great. "
Updated, dog-friendly cottage with bay views, wraparound deck & EV charger

Stunning Views of CA Coast : Beautifully Remodeled Home

9.8 out of 10, Exceptional, (334)
"We will stay again!"
Stunning Views of CA Coast : Beautifully Remodeled Home

Bodega Bay - Magical Ocean Front View- Doesn’t get better than this!!

9.8 out of 10, Exceptional, (165)
"We will definitely be back...absolutely Heavenly"
The price is CA $962
CA $1,721 total
includes taxes & fees
Apr 23 - Apr 24
Bodega Bay - Magical Ocean Front View- Doesn’t get better than this!!

Beautiful South Harbor Home with Great Ocean Views Point View House

9.6 out of 10, Exceptional, (139)
"Perfect place for our family reunion, we loved the views, short walk to the beach, short drive to church store and beach, we would definitely go back! "
Beautiful South Harbor Home with Great Ocean Views Point View House
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.
Don't see what you're looking for?
See all available properties in Chalk Hill
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Chalk Hill you may be interested in

Holiday Inn Windsor Wine Country by IHG

3.0 star property
9.0 out of 10, Wonderful, (975)
"Great stay for families, good value!"
The price is CA $165
CA $188 total
includes taxes & fees
Apr 28 - Apr 29
Holiday Inn Windsor Wine Country by IHG

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Overall a great place to stay, friendly staff & good breakfast. "
The price is CA $187
CA $213 total
includes taxes & fees
Apr 28 - Apr 29
Holiday Inn Express® Windsor Sonoma Wine Country by IHG

Hampton Inn & Suites Windsor - Sonoma Wine Country

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Great stay and service near everything!"
The price is CA $211
CA $240 total
includes taxes & fees
May 11 - May 12
Hampton Inn & Suites Windsor - Sonoma Wine Country
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.