Photo by William E Berry Jr.

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Check prices for these dates

Next weekend
18 Rab. II - 20 Rab. II
In two weeks
25 Rab. II - 27 Rab. II
In one month
9 Jum. I - 11 Jum. I
In two months
6 Jum. II - 8 Jum. II

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

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)
"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
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)
"Overall great stay for the family and friends. Communication was easy and available as needed. One issue that arose with people in the studio was handled expeditiously by Dave. Great location and layout for kids and adults to have separate areas. Would highly recommend "
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults
Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (33)
"Great stay"
Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,
BearHaus- HUGE Hot Tub, FirePit
Pool

BearHaus- HUGE Hot Tub, FirePit

9.6 out of 10, Exceptional, (5)
"Great property - excellent hosts. Close to mountain and restaurants"
The price is SAR 1,014
SAR 3,165 total
includes taxes & fees
20 Apr - 21 Apr
BearHaus- HUGE Hot Tub, FirePit
"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)
"Had a lovely weekend with "
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
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
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)
"Our family of grandparents, parents and young adults enjoyed the house for 3 nights. We skied at the golf course, had a long walk up the road and put together a difficult puzzle (took 3 days). We would have loved a larger table for the puzzle - we brought in one of our car's rear folding covers.The only complaint was the beds - they all have VERY firm mattresses.I told the owner that the toilet paper holder was not secured to the wall in the upstairs bathroom. "
Modern 4-Bedroom Mountain Retreat Minutes to Lake Rescue & Echo and Hiking
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 SAR 1,763
SAR 4,553 total
includes taxes & fees
13 Apr - 14 Apr
West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted ski rentals.
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 spent a great week in Weston. Great location to ski Stratton. Hosts were very responsive. Would def go back."
The price is SAR 935
SAR 2,195 total
includes taxes & fees
14 Apr - 15 Apr
Cozy Creekside Chalet centrally located near 4 ski resorts
Calling all hikers, bikers, golfers, kayakers, swimmers for summer fun
Property grounds

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

2.0 star property
10.0 out of 10, Exceptional, (11)
"We stayed at the Bigfoot Chalet for a last-minute ski trip, and we had a wonderful stay. Home was clean, comfortable, and well-appointed. Convenient to Killington - about a 25-30 min - and a lovely place to unwind at the end of a long day of skiing. We would love to return! "
The price is SAR 747
SAR 1,787 total
includes taxes & fees
30 Apr - 1 May
Calling all hikers, bikers, golfers, kayakers, swimmers for summer fun
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!
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)
"This house was perfect for two families with teens spending a weekend at Okemo. The mountain was a short drive away. The beds were comfortable and everything was clean. It was nice to have a big table that fit everyone for meals. The hot tub was a nice treat after skiing. It was so convenient that we could bring our dog too. The owner was very responsive to questions. We had a great weekend!"
Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!
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

The price is SAR 846
SAR 2,963 total
includes taxes & fees
13 Apr - 14 Apr
Spaceship Chalet Killington: Your Groovy Ski Home, Close to the slopes, bars and restaurants
Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo
Aerial view

Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo

10.0 out of 10, Exceptional, (10)
"The house is beautiful and we enjoyed our stay! Just need a full length mirror in a bedroom otherwise perfect ski property!"
Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo
Mountain View Chalet Fabulous views large entertaining area just off Killington Road
Fridge, microwave, stovetop, dishwasher

Mountain View Chalet Fabulous views large entertaining area just off Killington Road

Mountain View Chalet Fabulous views large entertaining area just off Killington Road
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 SAR 2,560
SAR 5,808 total
includes taxes & fees
13 Apr - 14 Apr
Bigelow Chalet at Killington: 8BR/4.5 BA Pet Friendly Home w/ Hot Tub, Fireplace.
Falcon House: VT Modern Chalet w/Sauna on 60 Acres | Hiking | Bike to Village
Fridge, microwave, oven, stovetop

Falcon House: VT Modern Chalet w/Sauna on 60 Acres | Hiking | Bike to Village

10.0 out of 10, Exceptional, (68)
"The house was very clean and tidy. Kat was great at communicating and making sure we had everything we needed!"
Falcon House: VT Modern Chalet w/Sauna on 60 Acres | Hiking | Bike to Village
Okemo 6 Bedroom Chalet.
Smart TV, fireplace, video games, stereo

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.
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)
"This is our second year staying at this beautiful home. We love the space and amenities, not to mention the location to the mountain. The owners have been very accommodating and communicative. Overall, a wonderful stay for our group of families and hope to return again when we come back to Ludlow."
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails
Northeast Passage Chalet is a cozy and warm. Wonderful hot tub on the deck and a great big stone fireplace.
Property grounds

Northeast Passage Chalet is a cozy and warm. Wonderful hot tub on the deck and a great big stone fireplace.

8.8 out of 10, Excellent, (5)
"Not as described "
Northeast Passage Chalet is a cozy and warm. Wonderful hot tub on the deck and a great big stone fireplace.
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 Windsor

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Fridge, microwave, oven, stovetop

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (42)
"This property was perfectly situated for ski on ski off accessibility. It had plenty of room for four adults. We also enjoyed the Sauna after skiing. The host Ryan was very easy to deal with and the check in/out process was simple and efficient. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Mountain Green
Indoor pool

Mountain Green

2.0 star property
6.4 out of 10, (9)
"We love the place very much. Clean and cozy, efficient communication. A home away from home, that we call the place we stayed. We would be happy to be back again. "
The price is SAR 815
SAR 1,093 total
includes taxes & fees
24 Apr - 25 Apr
Mountain Green
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Outdoor dining

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (205)
"this cabin was absolutely adorable. The kitchen was great size living room, small but cozy. The only thing I think we would like to call out is that the stairs to the loft bedrooms are quite steep be very careful. Everything was impeccably, clean, very cozy and comfortable. Hot tub was perfect and all instructions for both of the hot tub and exit were clear and easy to read."
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
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.