Photo by William E Berry Jr.

Search Chalets in Windsor

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Compare 47 Chalets in Windsor with updated reviews, rates, and availability.

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 SAR 743
SAR 1,781 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

10.0 out of 10, Exceptional, (1)
"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

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

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 SAR 649
SAR 1,777 total
includes taxes & fees
14 Jun - 15 Jun
Cozy Creekside Chalet centrally located near 4 ski resorts

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

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

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

10.0 out of 10, Exceptional, (1)
The price is SAR 1,056
SAR 3,072 total
includes taxes & fees
1 Jun - 2 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

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

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

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!

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.

2.0 star property
The price is SAR 1,762
SAR 4,447 total
includes taxes & fees
1 Jun - 2 Jun
West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted ski rentals.

BearHaus Central AC, HUGE Hot Tub, Awesome FirePit

9.6 out of 10, Exceptional, (5)
"Beautiful kitchen, great amenities, awesome location!"
The price is SAR 3,053
SAR 5,546 total
includes taxes & fees
2 Jun - 3 Jun
BearHaus Central AC, HUGE Hot Tub, Awesome FirePit

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 SAR 2,558
SAR 5,841 total
includes taxes & fees
1 Jun - 2 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

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!

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.

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.

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.

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.
Save an average of 15% on thousands of hotels when you're signed in