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Featured Condo Rentals in Chalk Hill and around

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"
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
WorldMark Windsor - 2 Bedroom Accessible
Exterior

WorldMark Windsor - 2 Bedroom Accessible

2.0 star property
10.0 out of 10, Exceptional, (1)
"Nice"
WorldMark Windsor - 2 Bedroom Accessible
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
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
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

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
WorldMark Windsor - 2 Bedroom Twin
Exterior

WorldMark Windsor - 2 Bedroom Twin

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
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
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
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
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
Wine Country Beautiful Worldmark 2Bedroom Resort
Outdoor dining

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
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
Wellington by Avantstay Secluded Wine Country Estate w/ Gorgeous Mtn Views
Interior

Wellington by Avantstay Secluded Wine Country Estate w/ Gorgeous Mtn Views

3.5 star property
Wellington by Avantstay Secluded Wine Country Estate w/ Gorgeous Mtn Views
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
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

Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton

Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton

10/10 Excellent
"It was pretty, the kids love the pool. Except that they let us wait for 1.5 hr to check in, when in fact we are there 4pm on scheduled check in. Other building was stinky not sure maybe it got smoking room. Otherwise we enjoyed our stay"
Liezl 1-night trip
Posted 9 hours ago
Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton