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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Browse Select Chalk Hill Condo Rentals

WorldMark Windsor - 2 Bedroom Accessible
Exterior

WorldMark Windsor - 2 Bedroom Accessible

2.0 star property
10.0 out of 10, Exceptional, (2)
"The condo was exactly as described and the queen murphy bed was comfortable. The condo was close to Santa Rosa! "
WorldMark Windsor - 2 Bedroom Accessible
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Exterior

Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6

9.2 out of 10, Wonderful, (43)
"Very well maintained"
The price is £436
includes taxes & fees
5 Aug - 6 Aug
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Vino Blanco by Avantstay Private Wine Country Home w/ Mtn Views & Deck
House (4 Bedrooms) | Interior

Vino Blanco by Avantstay Private Wine Country Home w/ Mtn Views & Deck

3.5 star property
Vino Blanco by Avantstay Private Wine Country Home w/ Mtn Views & Deck
WorldMark Windsor - 2 Bedroom
Exterior

WorldMark Windsor - 2 Bedroom

2.0 star property
8.6 out of 10, Excellent, (8)
"WorldMark Windsor is a perfect location for wine tasting in the Sonoma area and easy access to the Redwoods and Pacific Coast. We appreciate the amenities as well - full, sized kitchen, 2 bedrooms and 2 full baths. We will stay here again!"
WorldMark Windsor - 2 Bedroom
WorldMark Windsor - 2 Bedroom Twin
Exterior

WorldMark Windsor - 2 Bedroom Twin

8.0 out of 10, Very good, (1)
"Great property & comfortable accommodations. Parking was an issue at night, as its a huge complex. Check in was typical timeshare sales funnel, just be prepared to dodge them. Even still, I'd stay here again"
WorldMark Windsor - 2 Bedroom Twin
León by Avantstay Private Breathtaking Character Cottage w/ Pool & Hot Tub
Outdoor pool

León by Avantstay Private Breathtaking Character Cottage w/ Pool & Hot Tub

3.5 star property
10.0 out of 10, Exceptional, (1)
"Beautiful home with excellent set up. Spacious, comfortable and in a safe private location. We used the hot tub as it was winter when we came and it was wonderful. Everything was very clean and in working condition. "
León by Avantstay Private Breathtaking Character Cottage w/ Pool & Hot Tub
WorldMark Windsor - 2 Bedroom Twin
Exterior

WorldMark Windsor - 2 Bedroom Twin

2.0 star property
8.0 out of 10, Very good, (2)
"Nice. "
WorldMark Windsor - 2 Bedroom Twin
Great Wine Country and Golfing Resort Getaway!!
Outdoor dining

Great Wine Country and Golfing Resort Getaway!!

8.8 out of 10, Excellent, (3)
"The property was very clean and easy to get around. They offered many amenities and have a very nice outdoor area to hang out. "
Great Wine Country and Golfing Resort Getaway!!
WorldMark Windsor - 2 Bedroom Twin
Exterior

WorldMark Windsor - 2 Bedroom Twin

10.0 out of 10, Exceptional, (1)
"Exactly as described. Comfortable, clean and quiet"
WorldMark Windsor - 2 Bedroom Twin
Mataro by Avantstay Large & Elegant Home in Santa Rosa w/ Hot Tub & Games
Terrace/patio

Mataro by Avantstay Large & Elegant Home in Santa Rosa w/ Hot Tub & Games

3.5 star property
2.0 out of 10, (1)
"Property canceled our stay two days before our arrival. Awful communication and still trying to get our money back even though Avantstay canceled our accommodations on us!"
Mataro by Avantstay Large & Elegant Home in Santa Rosa w/ Hot Tub & Games
Stylish Condo Steps from St. Helena Wineries & Downtown
Property grounds

Stylish Condo Steps from St. Helena Wineries & Downtown

9.6 out of 10, Exceptional, (5)
"This is a solid value with a great location in St Helena!"
Stylish Condo Steps from St. Helena Wineries & Downtown
Tranquil 2-bedroom condo in Healdsburg with AC, WiFi
Property grounds

Tranquil 2-bedroom condo in Healdsburg with AC, WiFi

Tranquil 2-bedroom condo in Healdsburg with AC, WiFi
Black Oak by Avantstay Modern & Chic Santa Rosa Hideaway With Pool Table, & Fire Pit
Interior

Black Oak by Avantstay Modern & Chic Santa Rosa Hideaway With Pool Table, & Fire Pit

3.5 star property
Black Oak by Avantstay Modern & Chic Santa Rosa Hideaway With Pool Table, & Fire Pit
WorldMark Windsor - 1 Bedroom Accessible
Exterior

WorldMark Windsor - 1 Bedroom Accessible

2.0 star property
10.0 out of 10, Exceptional, (1)
"We were celebrating our 20th wedding anniversary and enjoyed our stay. We were gifted a nice bottle of wine for our anniversary which was a pleasant surprise!"
WorldMark Windsor - 1 Bedroom Accessible
Charming 2-bedroom condo in enchanting Healdsburg with WiFi, AC
Dining

Charming 2-bedroom condo in enchanting Healdsburg with WiFi, AC

Charming 2-bedroom condo in enchanting Healdsburg with WiFi, AC
Cotati Station condo with Garage and A/C
Interior

Cotati Station condo with Garage and A/C

2.0 star property
10.0 out of 10, Exceptional, (1)
"We really enjoyed this stay (one month) and Kristy was so helpful and replied to any questions very quickly! The unit was very clean and had a lot of space. It is a tri-level so there were stairs. Perfect location, close to work while we looked for a permanent home. Would highly recommend this VRBO! "
Cotati Station condo with Garage and A/C
Wine Country Beautiful Worldmark 2Bedroom Resort
TV, fireplace

Wine Country Beautiful Worldmark 2Bedroom Resort

9.4 out of 10, Exceptional, (65)
"A comfortable, up-to-date alternative to hotels in the area, with plenty of resort-style and family-friendly amenities."
Wine Country Beautiful Worldmark 2Bedroom Resort
WorldMark Windsor - 1 Bedroom
Exterior

WorldMark Windsor - 1 Bedroom

2.0 star property
9.0 out of 10, Wonderful, (4)
"Very well maintained and responsive staff"
WorldMark Windsor - 1 Bedroom
Charming 1 bedroom Cabin with King bed, Queen Sofa Sleeper, WIFI, Kitchen, Deck
Fridge, microwave, oven, stovetop

Charming 1 bedroom Cabin with King bed, Queen Sofa Sleeper, WIFI, Kitchen, Deck

Charming 1 bedroom Cabin with King bed, Queen Sofa Sleeper, WIFI, Kitchen, Deck
Visit Beautiful California Wine Country with Style - River, Coast, Redwoods
Exterior

Visit Beautiful California Wine Country with Style - River, Coast, Redwoods

Visit Beautiful California Wine Country with Style - River, Coast, Redwoods
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

The Sandman Santa Rosa Sonoma, Ascend Hotel Collection

The Sandman Santa Rosa Sonoma, Ascend Hotel Collection

10/10 Excellent
"I very much enjoyed my stay at Sandman Hotel. Room was clean and in very good condition, refrigerator and microwave worked, and bed was comfortable. Five stars!"
Trisha 3-night trip
Posted 1 day ago
The Sandman Santa Rosa Sonoma, Ascend Hotel Collection