Photo by Rick Alvarez

Holiday Rentals in Chalk Hill

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Check prices for these dates

Our top choices for Chalk Hill holiday rentals

1. Vineyard View Retreat • Fire Pit • Wine Tasting Perks

Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Healdsburg
9.8 out of 10, Exceptional, (19 reviews)
"Great place. Quiet, very clean, close to Healdsburg, grocery stores, etc. Very helpful and nice host. We would definitely stay here again when in the area."
United States
Mark R.
The price is €338
includes taxes & fees
2 Dec - 3 Dec
Vineyard View Retreat • Fire Pit • Wine Tasting Perks

2. Sauna, Cold Plunge & Fire Pit Near Wineries

Sauna, Cold Plunge & Fire Pit Near Wineries
Windsor
10.0 out of 10, Exceptional, (1 review)
"Very accommodating home with all the essentials. Awesome backyard for the dogs, great location and communication. "
United States
Keri S.
The price is €829
includes taxes & fees
8 Nov - 9 Nov
Sauna, Cold Plunge & Fire Pit Near Wineries

3. Hideaway Cottages

Hideaway Cottages
2.0 star property
Calistoga
The price is €256
includes taxes & fees
9 Nov - 10 Nov
Hideaway Cottages

4. Wildhaven Sonoma Glamping

Wildhaven Sonoma Glamping
1.0 star property
Healdsburg
9.2 out of 10, Wonderful, (139 reviews)
"Nice place to be in with your dog, very good for comfortable stay"
United States
NEERJA
The price is €100
includes taxes & fees
7 Dec - 8 Dec
Wildhaven Sonoma Glamping

5. Mandala Springs Wellness Retreat Center

Mandala Springs Wellness Retreat Center
3.5 star property
Cobb
8.8 out of 10, Excellent, (39 reviews)
"Waterfront cabins were amazing. The location and wildlife were serene, fantastic place to stay."
United States
Carmino
The price is €144
includes taxes & fees
8 Dec - 9 Dec
Mandala Springs Wellness Retreat Center

6. The Ranch at Lake Sonoma

The Ranch at Lake Sonoma
1.0 star property
Geyserville
9.0 out of 10, Wonderful, (10 reviews)
"Enjoyed my stay"
United States
Epeli
The price is €80
includes taxes & fees
14 Nov - 15 Nov
The Ranch at Lake Sonoma

7. 2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (32 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 €245
includes taxes & fees
16 Nov - 17 Nov
2 Hidden Wine Country Gem Upstairs Unit

8. Cozy Wine Country Guesthouse with Private Pool & Yard

Cozy Wine Country Guesthouse with Private Pool & Yard
Santa Rosa
10.0 out of 10, Exceptional, (39 reviews)
"Wonderful stay!"
United States
Adam C.
The price is €307
includes taxes & fees
9 Nov - 10 Nov
Cozy Wine Country Guesthouse with Private Pool & Yard

9. Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA
Santa Rosa
9.8 out of 10, Exceptional, (83 reviews)
"Our stay was pleasant, the place was exceptionally clean and the owners were very helpful."
United States
joanne h.
The price is €370
includes taxes & fees
8 Nov - 9 Nov
Wine Country Cottage in downtown Santa Rosa, CA

10. Private Lofted Downtown Studio

Private Lofted Downtown Studio
Sebastopol
9.8 out of 10, Exceptional, (55 reviews)
"Very cute and luxurious!! We really enjoyed our stay and great proximity to downtown. "
United States
Yvonne L.
The price is €416
includes taxes & fees
18 Nov - 19 Nov
Private Lofted Downtown Studio

11. 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, (49 reviews)
"We stayed here 15 years ago , same bedspreads and no new updates . We love it for its cozy feeling , and love the peacefulness of staying in Calistoga. We walked across the street for an awesome dinner at Sam’s Social club , walked down the street to shop and cruise around this quaint town . It’s a high price point , but we always enjoy our time there . I worry that if they ever remodel this place , the price point will be more than what it’s worth a night , for which I don’t believe would be...
United States
William
The price is €414
includes taxes & fees
9 Nov - 10 Nov
Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown

12. Escape to wine country in your independent cottage in downtown Calistoga

Escape to wine country in your independent cottage in downtown Calistoga
Calistoga
9.8 out of 10, Exceptional, (8 reviews)
"We absolutely loved our stay! The home was clean, quiet, private, and incredibly convenient. We were especially grateful that the hosts allowed our three dogs, which made this trip extra special. We spent a few days enjoying Calistoga and Napa before taking our sweet pup to UC Davis, and this was the perfect place for us. As empty nesters, we love traveling with our three dogs and hope to stay here again someday!"
United States
Jennifer G.
The price is €414
includes taxes & fees
9 Nov - 10 Nov
Escape to wine country in your independent cottage in downtown Calistoga

13. Wine Country Farmhouse on a Horse Ranch w/ Hot Tub

Wine Country Farmhouse on a Horse Ranch w/ Hot Tub
Santa Rosa
10.0 out of 10, Exceptional, (75 reviews)
"The property was beautiful and the beds were so comfy! The property manager was very friendly and responsive. "
United States
Abigail M.
The price is €417
includes taxes & fees
9 Nov - 10 Nov
Wine Country Farmhouse on a Horse Ranch w/ Hot Tub

14. Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed

Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed
Calistoga
10.0 out of 10, Exceptional, (5 reviews)
"Property is beautiful rooms are so clean. Service was incredible."
United States
Paul L.
The price is €414
includes taxes & fees
9 Nov - 10 Nov
Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed

15. Sebastopol Lux Walk toTown Guest Suite

Sebastopol Lux Walk toTown Guest Suite
Sebastopol
9.4 out of 10, Exceptional, (8 reviews)
"Beautiful place. Bed was extremely comfortable. Overall environment was pleasant. Coffee set up was good for me as a black coffee drinker. We would stay again and would happily recommend it to others."
United States
Brad
The price is €212
includes taxes & fees
16 Nov - 17 Nov
Sebastopol Lux Walk toTown Guest Suite

16. Charming Wine Country Home w/Hot Tub near Downtown

Charming Wine Country Home w/Hot Tub near Downtown
Santa Rosa
9.8 out of 10, Exceptional, (21 reviews)
"Very clean, convenient for our purposes, thank you"
United States
Howard
The price is €514
includes taxes & fees
9 Nov - 10 Nov
Charming Wine Country Home w/Hot Tub near Downtown

17. Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts

Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts
Northwest Santa Rosa
10.0 out of 10, Exceptional, (85 reviews)
"Great Home. Decent value.Didn’t realize the street were gonna be so compacted with houses very small streets"
United States
Melissa M.
The price is €538
includes taxes & fees
8 Nov - 9 Nov
Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts

18. Serenity at the Russian River

Serenity at the Russian River
Mirabel Heights
10.0 out of 10, Exceptional, (44 reviews)
"We had a great stay. The house was clean, the beds were comfy and a very convenient location. Just wish there was an ironing board. I would definitely recommend staying here."
United States
Patricia A.
The price is €461
includes taxes & fees
12 Nov - 13 Nov
Serenity at the Russian River

19. 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 €312
includes taxes & fees
9 Nov - 10 Nov
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

20. Modern Country Home Near Downtown & Bike Trail

Modern Country Home Near Downtown & Bike Trail
Sebastopol
10.0 out of 10, Exceptional, (9 reviews)
"Very clean and lots of you nearby"
United States
Santo Q.
The price is €444
includes taxes & fees
9 Nov - 10 Nov
Modern Country Home Near Downtown & Bike Trail
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.

Find holiday rentals that suit your style

Find out more about Chalk Hill

Everything you need to know about Chalk Hill holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chalk Hill holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chalk Hill holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chalk Hill holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chalk Hill holiday rentals we have selected for you start as low as €80 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chalk Hill rentals

At Expedia, we put the best Chalk Hill holiday 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 holiday.

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.

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