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Search Chalets in Windsor from CA $233

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Windsor Chalets

Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4
Situated in a lush environment, this cabin features a wooden deck and a steeply pitched roof.

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

9.6 out of 10, Exceptional, (48)
"Clean property, beautiful views, definitely would stay again! "
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4
Cozy Creekside Chalet centrally located near 4 ski resorts
Escape to a serene forest retreat with a cozy cabin featuring a charming front porch and balcony overlooking the surrounding trees.

Cozy Creekside Chalet centrally located near 4 ski resorts

10.0 out of 10, Exceptional, (12)
"We spent a great week in Weston. Great location to ski Stratton. Hosts were very responsive. Would def go back."
The price is CA $233
CA $633 total
includes taxes & fees
Sep 5 - Sep 6
Cozy Creekside Chalet centrally located near 4 ski resorts
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
Relax in a hot tub on a deck surrounded by serene winter scenery.

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

9.8 out of 10, Exceptional, (35)
"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
Spacious 5-bedroom chalet with AC and WiFi in charming Chester
Relax in a serene hot tub surrounded by a forested landscape.

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

10.0 out of 10, Exceptional, (4)
"Girls family weekend, relaxing, visiting and enjoying the hot tub."
Spacious 5-bedroom chalet with AC and WiFi in charming Chester
West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted ski rentals.
Relax in the hot tub surrounded by a wooden deck and lush trees.

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

2.0 star property
8.0 out of 10, Very good, (1)
"It was easy to check in and out and there was plenty of parking. There were also ACs in all of the bedrooms but 1. This was important since it was 90 degrees. We only wish the ice machine that was provided worked. The living room furniture, especially the couch, was amazingly comfy. We did a lot of bonding in that space. When we walked in on the first evening, there were some windows open, and there was a furry chicken nugget sitting on the arm of a chair though. The basement had bedrooms in...
The price is CA $646
CA $1,609 total
includes taxes & fees
Aug 10 - Aug 11
West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted ski rentals.
Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski
Exterior

Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski

10.0 out of 10, Exceptional, (23)
"House was great, we loved our stay. Definitely walk down the road and get pizza! It was our favorite dinner of our trip and absolutely delicious! "
Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski
Fall into Cozy at Bigfoot Chalet
Two-story cabin with a balcony and porch, featuring a red door and Adirondack chairs.

Fall into Cozy at Bigfoot Chalet

2.0 star property
10.0 out of 10, Exceptional, (13)
"Excellent week at a cozy property, convenient to Killington and Okemo. Easy check in and check out; highly responsive and helpful host. Would recommend to those looking for a great VT escape."
The price is CA $288
CA $670 total
includes taxes & fees
Sep 1 - Sep 2
Fall into Cozy at Bigfoot Chalet
Cozy chalet minutes from Okemo Mtn & VAST
Relax on the deck with comfortable Adirondack chairs, a small table, and a beautiful garden view.

Cozy chalet minutes from Okemo Mtn & VAST

2.0 star property
Cozy chalet minutes from Okemo Mtn & VAST
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults
Situated in a serene forest, this cabin offers a peaceful retreat amidst the snow-covered hills.

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

10.0 out of 10, Exceptional, (24)
"A terrific place. Highly recommended. We had a great family ski vacation."
The price is CA $1,375
CA $2,749 total
includes taxes & fees
Aug 10 - Aug 11
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!
Enjoy the scenic views from the upper balcony of this cozy cabin, featuring a brick chimney and windows on both levels.

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!
Killington Chalet - Great Space and Location!
Stunning two-story home surrounded by mature trees in a peaceful wooded area.

Killington Chalet - Great Space and Location!

9.6 out of 10, Exceptional, (15)
"Our group of 10 friends had a wonderful stay at the Chalet. Great location to the mountain and local restaurants and entertainment. Plenty of room to spread out and great communal area as well. "
Killington Chalet - Great Space and Location!
Modern Chalet by Mt. Sunapee
Relax on the elevated deck with a view of the surrounding landscape.

Modern Chalet by Mt. Sunapee

Modern Chalet by Mt. Sunapee
Log Home# w/ Incomparable Peace, Serenity, Privacy And The First Class Amenities
Cozy cabin with a balcony and rustic charm, offering a peaceful retreat.

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

10.0 out of 10, Exceptional, (107)
"The house was equipped with everything we needed! Cant wait to come back! "
Log Home# w/ Incomparable Peace, Serenity, Privacy And The First Class Amenities
Falcon House: VT Modern Chalet w/Sauna on 25 Acres - Hike - Bike to Village
Escape to a secluded cabin nestled in a lush forest, offering a tranquil retreat with easy access.

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

10.0 out of 10, Exceptional, (69)
"We had a wonderful relaxing time at Falcon house. The house was clean, just as listed, and had everything we needed to make for an enjoyable relaxing time. Really enjoyed the scenery and walking around Woodstock."
Falcon House: VT Modern Chalet w/Sauna on 25 Acres - Hike - Bike to Village
Okemo 6 Bedroom Chalet.
Guests can enjoy a covered porch with large windows and a beautiful winter view.

Okemo 6 Bedroom Chalet.

9.4 out of 10, Exceptional, (23)
"We were up for a weekend in February. Perfect place. Plenty of beds. The hot tub was a bonus. Excellent communication by the hosts. "
Okemo 6 Bedroom Chalet.
South View Chalet!
Situated beside a serene pond, this charming house offers a tranquil atmosphere with a symmetrical facade and lush surroundings.

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!
Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,
Situated in a winter wonderland, this charming two-story house boasts a steeply pitched roof and a prominent brick chimney.

Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,

9.6 out of 10, Exceptional, (33)
"We had a fabulous stay here. Owner was v communicative and accommodating."
Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,
BearHaus Central AC, HUGE Hot Tub, Awesome FirePit
Chalet-style building with a spacious balcony and lush surroundings, offering a serene escape.

BearHaus Central AC, HUGE Hot Tub, Awesome FirePit

9.6 out of 10, Exceptional, (5)
"Great property - excellent hosts. Close to mountain and restaurants"
The price is CA $480
CA $1,317 total
includes taxes & fees
Sep 2 - Sep 3
BearHaus Central AC, HUGE Hot Tub, Awesome FirePit
Bigelow Chalet at Killington: 8BR/4.5 BA Pet Friendly Home w/ Hot Tub, Fireplace.
Guests can unwind in this serene outdoor space featuring a hot tub and wooden deck with a pergola.

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 CA $938
CA $2,130 total
includes taxes & fees
Aug 10 - Aug 11
Bigelow Chalet at Killington: 8BR/4.5 BA Pet Friendly Home w/ Hot Tub, Fireplace.
Cozy Chalet 2 min drive to Okemo Base and Downtown, and 5 min to Jackson Gore.
Situated in a winter wonderland, this cabin offers a cozy outdoor seating area with a fire pit.

Cozy Chalet 2 min drive to Okemo Base and Downtown, and 5 min to Jackson Gore.

Cozy Chalet 2 min drive to Okemo Base and Downtown, and 5 min to Jackson Gore.
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 Windsor Hotel Reviews

The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"Great place to stay, so close to the mountain, rode my bike all weekend. Clean comfortable room and the staff treated us like family. Highly recommended. Thanks!"
john 1-night trip
Posted 3 days ago
The Mountain Inn at Killington