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Compare 30 Condo Rentals in Chalk Hill with updated reviews, rates, and availability.

Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Dining
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
9.2 out of 10, Wonderful, (39)
"Worldmark Windsor is an excellently maintained resort near a neighborhood with a lot of walking options. Close to many wineries, it is a great place to stay. The condo was clean and had a great kitchen. I would definitely stay here again when visiting the wine country."
The price is AED 845
AED 2,070 total
includes taxes & fees
3 Nov - 4 Nov
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Worldmark Windsor/Healdsburg Wine country 3BR 2BATH Sleeps8 Instabook!!
Pool
Worldmark Windsor/Healdsburg Wine country 3BR 2BATH Sleeps8 Instabook!!
9.2 out of 10, Wonderful, (7)
"Think of this place as a home away from home. It has everything you need to cook meals and fridge, dishwasher, washer and dryer, oven with some baking sheets. I would recommend that if you are going to be doing the majority of cooking there to bring your own oils, spices, aluminum foil and plastic wrap. The unit was immaculate! All the units have a grill and patio furniture. The bathrooms were super clean and spacious! My unit had an extra bed in the living room, Murphy bed."
Worldmark Windsor/Healdsburg Wine country 3BR 2BATH Sleeps8 Instabook!!
Worldmark Windsor, Beautiful Wine Country 2BR 2Bath Sleep6 Resort Condos
Worldmark Windsor, Beautiful Wine Country 2BR 2Bath Sleep6 Resort Condos
3.0 star property
8.4 out of 10, Very Good, (8)
"Enjoyed location and proximity to Healdsburg."
Worldmark Windsor, Beautiful Wine Country 2BR 2Bath Sleep6 Resort Condos
Wine Country Beautiful Worldmark 2Bedroom Resort
Pool
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
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
Wellington by Avantstay Secluded Wine Country Estate w/ Gorgeous Mtn Views
Exterior
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
Mataro by Avantstay Large & Elegant Home in Santa Rosa w/ Hot Tub & Games
Living area
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, Beautiful Wine Country 2BR 2Bath Sleeps6 NICE!
Worldmark Windsor, Beautiful Wine Country 2BR 2Bath Sleeps6 NICE!
9.6 out of 10, Exceptional, (27)
"Very nice and convenient place. Only hiccup was checking in. It was to be available at 4 pm. Did not get our room till 7 pm"
Worldmark Windsor, Beautiful Wine Country 2BR 2Bath Sleeps6 NICE!
Stylish Condo Steps from St. Helena Wineries & Downtown
Interior
Stylish Condo Steps from St. Helena Wineries & Downtown
10.0 out of 10, Exceptional, (3)
"I could not have asked for a better location. Quiet neighborhood, clean, comfy beds and linens, and it looks just like the pictures. We walked to Model bakery in the mornings for their wonderful English muffins. Found a hidden gem tasting room called Hayfork right around the corner (behind Clif Family)that does free tastings on Fridays! Excellent wine! And of course we got in a burger at Gotts. The location makes it easy to walk to Main Street with lots of restaurants and shopping. There...
Stylish Condo Steps from St. Helena Wineries & Downtown
WorldMark Windsor - 1 Bedroom
Windsor_pool_3_S
WorldMark Windsor - 1 Bedroom
2.0 star property
9.0 out of 10, Wonderful, (2)
"The condo was very clean and had everything needed for a relaxing stay. The pool was also wonderful with no overcrowding! "
WorldMark Windsor - 1 Bedroom
Visit Beautiful California Wine Country with Style - River, Coast, Redwoods
Pool
Visit Beautiful California Wine Country with Style - River, Coast, Redwoods
Visit Beautiful California Wine Country with Style - River, Coast, Redwoods
WorldMark Windsor - 2 Bedroom Twin
Windsor_pool_S
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
Windsor_pool_3_S
WorldMark Windsor - 2 Bedroom
2.0 star property
9.6 out of 10, Exceptional, (4)
"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
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
Vino Blanco by Avantstay Private Wine Country Home w/ Mtn Views & Deck
Outdoor dining
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
Estrella by Avantstay Secluded Spanish-style Estate on 7 Acres of Vineyards
Pool
Estrella by Avantstay Secluded Spanish-style Estate on 7 Acres of Vineyards
3.5 star property
Estrella by Avantstay Secluded Spanish-style Estate on 7 Acres of Vineyards
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
Bennett Valley home is a great location to explore Sonoma Valley.
Exterior detail
Bennett Valley home is a great location to explore Sonoma Valley.
Bennett Valley home is a great location to explore Sonoma Valley.
Charming 2-bedroom condo in enchanting Healdsburg with WiFi, AC
Living area
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
Main living room
Cotati Station condo with Garage and A/C
2.0 star property
Cotati Station condo with Garage and A/C
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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

Cottage home near the Russian River; county parks; numerous wineries
Dining
Cottage home near the Russian River; county parks; numerous wineries
10.0 out of 10, Exceptional, (89)
"Great house, no issues. "
Cottage home near the Russian River; county parks; numerous wineries
Chalk Hill Cottage Close to Wineries
Chalk Hill Cottage Close to Wineries
9.8 out of 10, Exceptional, (24)
"The cottage is very nice and well appointed, with all the needed amenities and more! Very convenient location to visit local wineries and the town of Healdsburg. It was very easy to communicate with our hosts as well. We had a great stay!"
Chalk Hill Cottage Close to Wineries
Stunning Home with Pool, Hot Tub, Decks, & Gourmet Kitchen - Close to Wineries
Stunning Home with Pool, Hot Tub, Decks, & Gourmet Kitchen - Close to Wineries
9.2 out of 10, Wonderful, (88)
"Cleanliness could have been better ( lots of cobwebs and dead flies in the tub) but we enjoyed the property."
Stunning Home with Pool, Hot Tub, Decks, & Gourmet Kitchen - Close to Wineries
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.