Photo by Jennifer Hill

Chalk Hill Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Chalk Hill

Cottage home near the Russian River; county parks; numerous wineries
10.0 out of 10, Exceptional, (82)
"Stayed mid week for several days. Overall a very nice experience. Super clean and quiet!"
Cottage home near the Russian River; county parks; numerous wineries
Chalk Hill Cottage Close to Wineries
9.8 out of 10, Exceptional, (16)
"We loved our cottage. Very well appointed, furniture lovely, kitchen cute. A little dark because it's set into hill but fine with lights on. We'll go back."
Chalk Hill Cottage Close to Wineries
Stunning Home with Pool, Hot Tub, Decks, & Gourmet Kitchen - Close to Wineries
9.2 out of 10, Wonderful, (87)
"I stayed with family in August of 2023, there were 8 of us total. The house is beautiful and there are many places to hang out together in a group or spread out and find your own space. The house was well stocked with linens and dishes in the kitchen as well as games and some toys in the game room. It was a great stay with only a couple exceptions. There was no Verizon cell service. There was also no internet although it states in the listing that there is internet/Wi-Fi. Thankfully one person...
Stunning Home with Pool, Hot Tub, Decks, & Gourmet Kitchen - Close to Wineries
Save an average of 15% on thousands of hotels when you're signed in
Gable by AvantStay | Beautiful 3.5 Acre Oasis w/ Gorgeous Views, Pool & Hot Tub
10.0 out of 10, Exceptional, (5)
"Our stay was amazing, since the property was located in a picturesque hill side surrounded by majestic oaks. The property was specious and accommodating and served us perfectly with its charming unique Retro decor."
Gable by AvantStay | Beautiful 3.5 Acre Oasis w/ Gorgeous Views, Pool & Hot Tub
Safari West
2.0 star property
9.4 out of 10, Exceptional, (221)
"Great experience with a great staff "
The price is CA $647
CA $737 total
includes taxes & fees
Jul 7 - Jul 8
Safari West
Oceanfront - Hot Tub - Newly Remodeled Cottage
9.8 out of 10, Exceptional, (327)
"Just what my family of four needed. A cozy place with fantastic views, sea breeze, smell of salt water, and relaxation. The spa was a plus while watching the sunset! The property communication after reservation was wonderful, instructions for check in and check out were very simple, we arrived to a very clean home, kitchen was equipped, and beds (and pillows) were very comfy. We will be back, thank you!"
Oceanfront - Hot Tub - Newly Remodeled Cottage
COZY Bungalow--Dog-Friendly—Perfect for Couples!!!
9.4 out of 10, Exceptional, (135)
"It's just as advertised, comfy and on the water."
COZY Bungalow--Dog-Friendly—Perfect for Couples!!!
4.5 Bedrooms, 3 Baths, 2 Kitchens, 180 degree views and a 'Man Cave'
9.2 out of 10, Wonderful, (153)
"The property has amazing views and is in a great location. Easy walk to the beach and golf course. Plenty of space for a family to spread out. Teens loved the pool table and retro video game. Excellent hosts with detailed instructions to facilitate a great stay!"
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, (52)
"Words and pictures will never do this propery justice. You must see it to believe it!"
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella
Wagging Woods | 3 Gated Acres | Private Hot Tub | Dog-Friendly
8.6 out of 10, Excellent, (29)
"Beautiful location. Very clean. Awesome if you had a dog!"
Wagging Woods | 3 Gated Acres | Private Hot Tub | Dog-Friendly
St Helena ~ Best Views Over Both Famous Valleys ~ Blair Spangler Design Group
10.0 out of 10, Exceptional, (15)
"12 of us traveled to Napa for my 40th birthday and we had THE BEST trip ever. The accommodations were lovely, spacious, clean and luxurious. The concierge was so responsive and helpful. The chefs were fantastic. I'd highly recommend this property. As a frequent traveler, I've stayed in many luxury rentals and this was by far my favorite."
St Helena ~ Best Views Over Both Famous Valleys ~ Blair Spangler Design Group
Secluded home with private saltwater pool, spa & amazing view - dog-friendly
8.4 out of 10, Very good, (15)
"Great"
Secluded home with private saltwater pool, spa & amazing view - dog-friendly
Waterfront 2 Bed 2 bath, fireplace + INCREDIBLE VIEWS right on Bodega Bay!
9.4 out of 10, Exceptional, (307)
"Cute, little 2 BR unit that is part of 3. Right on the bay, I mean you could fish off the deck at high tide. A very steep driveway which makes getting onto Rt 1 a bit dicey. Hot water took about 4-5 minutes but great water pressure in front BR shower. WiFi is suitable for emails and surfing but uploads and downloads were a bit tough. The owner was responsive and helpful with suggestions. Many restaurants had limited hours. Great sunsets to be viewed from the deck."
The price is CA $476
CA $919 total
includes taxes & fees
Jul 10 - Jul 11
Waterfront 2 Bed 2 bath, fireplace + INCREDIBLE VIEWS right on Bodega Bay!
Lovely Home Near Beach w/Private W/D & Free WiFi - Panoramic Ocean Views Await
9.4 out of 10, Exceptional, (90)
"The property was as advertised. Very clean and tidy. everything you need in the kitchen for whipping up breakfast, lunch and dinner. We are tea drinkers and could find no kettle, but everthing else including a full spice cupboard was there. We'd definately stay again"
Lovely Home Near Beach w/Private W/D & Free WiFi - Panoramic Ocean Views Await
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
10.0 out of 10, Exceptional, (200)
"This is the perfect house to stay in with a large group! The hosts are great and very responsive. The house is beautiful and has plenty of bedrooms and bathrooms for everyone! The location could not be better and is right off the main road. Overall an amazing experience and would recommend to everyone!"
The price is CA $2,246
CA $2,881 total
includes taxes & fees
Jul 8 - Jul 9
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard
9.8 out of 10, Exceptional, (377)
"This is the 2nd time we've stayed and thoroughly enjoyed Aftermath. It's a peaceful, simple cottage with a coastline view that is stunning. Love the history with the place and many others have made it part of their history too."
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard
Comfort and Style in Our Queen Cottage
9.8 out of 10, Exceptional, (37)
"Lovely little set of well appointed cabins just a couple blocks from main street Calistoga. Communication and check-in was painless. Easy access, quiet and lovely. Would definitely stay again. Great place if you're traveling with other couples and want to be close but have your own place."
The price is CA $257
CA $347 total
includes taxes & fees
Jul 7 - Jul 8
Comfort and Style in Our Queen Cottage
Casa Loma - THE best Napa Valley Views at an amazing, modern 35 acre estate
10.0 out of 10, Exceptional, (114)
"Beautiful house to share with my husband and 5 of our friends. The house has everything you hope for and the host was excellent! Would def stay again and again!"
Casa Loma - THE best Napa Valley Views at an amazing, modern 35 acre estate
The St. Helena House - Within Walking Distance To Downtown. Permit # PL23-018
10.0 out of 10, Exceptional, (212)
"Beautiful, warm and welcoming! We all enjoyed our stay. Sitting outside in the evenings, enjoying our wine purchases from the day, overlooking a beautiful vineyard and valley. Loved the history, charm and character of this beautiful farm house."
The St. Helena House - Within Walking Distance To Downtown. Permit # PL23-018
Stunning Views of CA Coast : Beautifully Remodeled Home
9.8 out of 10, Exceptional, (305)
"We stayed here while going to our daughter’s wedding on their property in Bodega. It couldn’t have been more perfect! Comfortable beds. Clean & beautiful!"
Stunning Views of CA Coast : Beautifully Remodeled Home
Don't see what you're looking for?
See all available properties in Chalk Hill
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.

Chalk Hill Vacation Rental Travel Info

Vacation rentals
2
Popular accommodation
Chalk Hill private vacation homes

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

Holiday Inn Express® Windsor Sonoma Wine Country, an IHG Hotel
2.5 star property
8.8 out of 10, Excellent, (1006)
"Front desk was a great help! Check in was also easy"
The price is CA $229
CA $256 total
includes taxes & fees
Jul 7 - Jul 8
Holiday Inn Express® Windsor Sonoma Wine Country, an IHG Hotel
Holiday Inn Windsor Wine Country, an IHG Hotel
3.0 star property
9.0 out of 10, Wonderful, (591)
"."
The price is CA $206
CA $230 total
includes taxes & fees
Jul 14 - Jul 15
Holiday Inn Windsor Wine Country, an IHG Hotel
The Sandman Hotel
3.0 star property
8.2 out of 10, Very good, (1841)
"Management was very helpful."
The price is CA $142
CA $162 total
includes taxes & fees
Jul 24 - Jul 25
The Sandman Hotel
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chalk Hill. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Recent reviews of Chalk Hill properties
Expedia verified reviews