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Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 48 Chalets in Windsor with updated reviews, rates, and availability.

Calling all hikers, bikers, golfers, kayakers, swimmers for summer fun
Smart TV, DVD player, books

Calling all hikers, bikers, golfers, kayakers, swimmers for summer fun

2.0 star property
10.0 out of 10, Exceptional, (11)
"The place was nice, the hosts were really excellent and responsive- and the location is very nice. It’s not too far to go hiking, swimming or kayaking!!!"
The price is AED 727
AED 1,744 total
includes taxes & fees
5 Jun - 6 Jun
Calling all hikers, bikers, golfers, kayakers, swimmers for summer fun
Spacious 5-bedroom chalet with AC and WiFi in charming Chester
Fridge, microwave, oven, stovetop

Spacious 5-bedroom chalet with AC and WiFi in charming Chester

10.0 out of 10, Exceptional, (2)
"All the beds were comfortable and plenty of beds. The grounds are great and the deck is very nice. Its a Beautiful area. Very well maintained. We will differently go again. "
Spacious 5-bedroom chalet with AC and WiFi in charming Chester
Okemo Mountain Chalet W/ Hot Tub and Game Room
Exterior

Okemo Mountain Chalet W/ Hot Tub and Game Room

9.8 out of 10, Exceptional, (159)
"Great house, great host"
Okemo Mountain Chalet W/ Hot Tub and Game Room
Cozy Creekside Chalet centrally located near 4 ski resorts
Exterior

Cozy Creekside Chalet centrally located near 4 ski resorts

10.0 out of 10, Exceptional, (9)
"We had the best time at this cozy spot with some friends for a weekend - highly recommend!"
The price is AED 621
AED 1,724 total
includes taxes & fees
25 Jun - 26 Jun
Cozy Creekside Chalet centrally located near 4 ski resorts
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4
Smart TV, DVD player, books, stereo

Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4

9.8 out of 10, Exceptional, (44)
"Clean property, beautiful views, definitely would stay again! "
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails
Exterior

Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails

10.0 out of 10, Exceptional, (39)
"Noreen was very communicative and the house was great. Had everything we needed and more than enough room for 2 five person families. It was in a great location—quick drive to the mountain. "
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails
Log Home# w/ Incomparable Peace, Serenity, Privacy And The First Class Amenities
Fridge, microwave, oven, stovetop

Log Home# w/ Incomparable Peace, Serenity, Privacy And The First Class Amenities

10.0 out of 10, Exceptional, (107)
"What a great escape. Plenty of space for plenty of folks, beautifully designed. Dining room table is gorgeous. Hosts were quick to respond throughout the process, would come back."
Log Home# w/ Incomparable Peace, Serenity, Privacy And The First Class Amenities
Spaceship Chalet Killington: Your Groovy Ski Home, Close to the slopes, bars and restaurants
Interior

Spaceship Chalet Killington: Your Groovy Ski Home, Close to the slopes, bars and restaurants

10.0 out of 10, Exceptional, (1)
The price is AED 1,034
AED 2,962 total
includes taxes & fees
4 Jun - 5 Jun
Spaceship Chalet Killington: Your Groovy Ski Home, Close to the slopes, bars and restaurants
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
Outdoor spa tub

"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

9.8 out of 10, Exceptional, (34)
"We very much enjoyed our stay and the property is in excellent proximity to Killington/Pico."
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
Modern 4-Bedroom Mountain Retreat Minutes to Lake Rescue & Echo and Hiking
Private kitchen

Modern 4-Bedroom Mountain Retreat Minutes to Lake Rescue & Echo and Hiking

9.6 out of 10, Exceptional, (5)
"Roshanak was an excellent host and the place is beautiful. We love the location and its proximity to Okemo and the town. The property is gorgeous, we would book again."
Modern 4-Bedroom Mountain Retreat Minutes to Lake Rescue & Echo and Hiking
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults
Interior

Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults

10.0 out of 10, Exceptional, (24)
"We had 4 families with a range of kids from 16-5. The house was the perfect space to spread out to give everyone space and things to do! The house was clean and stocked with whatever you needed during the stay. We’ve done a lot of VRBO rentals and this was one of our best experiences! Plus, the trail was amazing to have in the backyard! "
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults
Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!
Property grounds

Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!

9.8 out of 10, Exceptional, (125)
"We found the hosts to be super helpful and friendly. Location was fantastic. We loved the hot tub and wood burning stove. It was a perfect stay for my extended family and I. The beds were also super comfortable-we slept great! We would definitely recommend this spot!"
Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!
West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted ski rentals.
Outdoor dining

West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted ski rentals.

2.0 star property
The price is AED 1,725
AED 4,297 total
includes taxes & fees
4 Jun - 5 Jun
West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted ski rentals.
BearHaus Central AC, HUGE Hot Tub, Awesome FirePit
Pool

BearHaus Central AC, HUGE Hot Tub, Awesome FirePit

9.6 out of 10, Exceptional, (5)
"Beautiful kitchen, great amenities, awesome location!"
The price is AED 992
AED 3,104 total
includes taxes & fees
4 Jun - 5 Jun
BearHaus Central AC, HUGE Hot Tub, Awesome FirePit
Bigelow Chalet at Killington: 8BR/4.5 BA Pet Friendly Home w/ Hot Tub, Fireplace.
Outdoor spa tub

Bigelow Chalet at Killington: 8BR/4.5 BA Pet Friendly Home w/ Hot Tub, Fireplace.

10.0 out of 10, Exceptional, (1)
"Awesome property and very responsive staff! Highly recommended. "
The price is AED 2,505
AED 5,670 total
includes taxes & fees
4 Jun - 5 Jun
Bigelow Chalet at Killington: 8BR/4.5 BA Pet Friendly Home w/ Hot Tub, Fireplace.
Falcon House: VT Modern Chalet w/Sauna on 25 Acres - Hike - Bike to Village
Fridge, microwave, oven, stovetop

Falcon House: VT Modern Chalet w/Sauna on 25 Acres - Hike - Bike to Village

10.0 out of 10, Exceptional, (68)
"House is beautiful, well stocked. Kat was exceptional as host; all my questions were promptly answered. Location is ideal"
Falcon House: VT Modern Chalet w/Sauna on 25 Acres - Hike - Bike to Village
South View Chalet!
Fridge, microwave, oven, stovetop

South View Chalet!

9.2 out of 10, Wonderful, (26)
"Great location and house. Perfect for large groups, there is plenty of space with multiple rooms so your group can spread out. Minutes to Killington mountain. "
South View Chalet!
Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.
Exterior

Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.

9.8 out of 10, Exceptional, (22)
"Victoria and Erica were wonderful hosts, everything was as expected and they were very responsive. Graciously arranged for extra snow plowing due to some pretty significant snowfall. Had room for three couples and kids, 10 in all, very comfortably. Would stay again!"
Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.
The Whimsical Chalet is a lovely cape on acres. Private setting less than 10 minutes to skiing.
Interior

The Whimsical Chalet is a lovely cape on acres. Private setting less than 10 minutes to skiing.

9.0 out of 10, Wonderful, (2)
"Stayed for a ski weekend and it was a nice quiet house on a quiet street but still situated close to the resorts."
The Whimsical Chalet is a lovely cape on acres. Private setting less than 10 minutes to skiing.
Okemo 6 Bedroom Chalet.
Smart TV, fireplace, video games, stereo

Okemo 6 Bedroom Chalet.

9.4 out of 10, Exceptional, (23)
"Hosts were great. Perfect location for skiing. However some messages from the host were not immediately received during the stay since they were sent through the app rather than direct to phone/text. Once we were checked in, didn’t frequently open the app during the weekend. To check messages. "
Okemo 6 Bedroom Chalet.
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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