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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Browse Select Chalk Hill Condo Rentals

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

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

9.2 out of 10, Wonderful, (40)
"The property was beautiful with many amenities. We would gladly stay there again. Close to freeway, and short drive to shopping, wineries, and breweries. Less than a 12 minute drive to Healdsburg. "
The price is £426
includes taxes & fees
5 May - 6 May
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
WorldMark Windsor - 2 Bedroom Twin
Exterior

WorldMark Windsor - 2 Bedroom Twin

2.0 star property
8.0 out of 10, Very good, (1)
"Very clean, convenient location, good facilities. Comfortable beds. Well equipped kitchen. Pool was a good size, hot tubs and pool open till 10 pm which was nice after a long day. I had only 2 issues, one that there was no free wifi. I was told before I booked that it would be free for my unit but was given no info. on how to access it for free, Apparently I needed some info. that no one was able to give me so I ended up having to pay for it. And the second of course is the pressure...
WorldMark Windsor - 2 Bedroom Twin
WorldMark Windsor - 2 Bedroom
Exterior

WorldMark Windsor - 2 Bedroom

2.0 star property
9.6 out of 10, Exceptional, (5)
"We needed to stay close to family and were able to spend time with them. Also getting to the airport lead so convenient. "
WorldMark Windsor - 2 Bedroom
WorldMark Windsor - 2 Bedroom Accessible
Exterior

WorldMark Windsor - 2 Bedroom Accessible

2.0 star property
WorldMark Windsor - 2 Bedroom Accessible
WorldMark Windsor - 2 Bedroom Twin
Exterior

WorldMark Windsor - 2 Bedroom Twin

WorldMark Windsor - 2 Bedroom Twin
Tranquil 2-bedroom condo in Healdsburg with AC, WiFi
Smart TV, books

Tranquil 2-bedroom condo in Healdsburg with AC, WiFi

Tranquil 2-bedroom condo in Healdsburg with AC, WiFi
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
Great Wine Country and Golfing Resort Getaway!!
Outdoor dining

Great Wine Country and Golfing Resort Getaway!!

8.0 out of 10, Very good, (2)
"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!!
Cotati Station condo with Garage and A/C
Private kitchen

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
Vino Blanco by Avantstay Private Wine Country Home w/ Mtn Views & Deck
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
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
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
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
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
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
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 - 3 Bedroom Penthouse
Exterior

WorldMark Windsor - 3 Bedroom Penthouse

2.0 star property
WorldMark Windsor - 3 Bedroom Penthouse
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
Clementine By Avantstay Bright Modern Retreat w/ Pool, Pool Table & Large Patio
Interior

Clementine By Avantstay Bright Modern Retreat w/ Pool, Pool Table & Large Patio

3.5 star property
Clementine By Avantstay Bright Modern Retreat w/ Pool, Pool Table & Large Patio
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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Other property types in Chalk Hill

Chalk Hill Cottage Close to Wineries
Exterior

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
Beach

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!!!
Beach

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

9.6 out of 10, Exceptional, (169)
"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!!!
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.