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Check prices for these dates

Next weekend
28 Mar - 30 Mar
In two weeks
4 Apr - 6 Apr
In one month
18 Apr - 20 Apr
In two months
16 May - 18 May

Compare 90 Chalets in Windham with updated reviews, rates, and availability.

New! Mt Snow Chalet w/land, privacy, relaxation
Outdoor dining

New! Mt Snow Chalet w/land, privacy, relaxation

9.0 out of 10, Wonderful, (4)
"Excellent location to skiing Spacious rooms Plenty of towels Kitchen stocked with appliances Close to market "
New! Mt Snow Chalet w/land, privacy, relaxation
Beautiful- Ski/Golf home, Hot tub, mins to MTN
Outdoor spa tub

Beautiful- Ski/Golf home, Hot tub, mins to MTN

8.4 out of 10, Very Good, (5)
"The cabin was very clean and matched expectations. We enjoyed the hot tub and the kitchen was well equipped. Emilio was very quick to reply to any questions. The only slight negatives were that the roads to the cabin were a bit dicey in the snow and the gas fireplace and TV were a bit confusing to operate. Overall a great stay and would definitely book again!"
Beautiful- Ski/Golf home, Hot tub, mins to MTN
Sunny Stratton Mountain Retreat: 5BD Modern Oasis w/Hot Tub, Pond, & BBQ Deck
Fridge, microwave, oven, stovetop

Sunny Stratton Mountain Retreat: 5BD Modern Oasis w/Hot Tub, Pond, & BBQ Deck

9.4 out of 10, Exceptional, (6)
"We were absolutely thrilled to experience a fresh powder drop during our stay, which was a delightful surprise in an otherwise dry season. The house surpassed all our expectations, providing the perfect haven for our large group. It was impeccably clean, incredibly warm, and featured an abundance of comfortable beds, all while being conveniently close to the mountain. A standout feature for us was the Tesla charger in the garage, which met our specific needs perfectly. We are already eagerly...
Sunny Stratton Mountain Retreat: 5BD Modern Oasis w/Hot Tub, Pond, & BBQ Deck
Beautiful Manchester VT Mountain Retreat w/Hot Tub
Fridge, microwave, oven, stovetop

Beautiful Manchester VT Mountain Retreat w/Hot Tub

10.0 out of 10, Exceptional, (32)
"We had 9 people in 2 family units staying at house. Then about another 6 that came each night to hang out. Plenty of room. 3 living room areas for everyone to spread out. Best stocked home EVER!!! There was literally everything and anything that we needed…..and then some. Inside sauna so cool. Unfortunately way too cold to go out and enjoy the hot tub. Decorations beyond beautiful. Owner very quick with communication. Highly recommend staying here. "
Beautiful Manchester VT Mountain Retreat w/Hot Tub
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, (106)
"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
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, (123)
"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!
Mid-Century Arty Chalet - 2 Min to Stratton Slopes
Smart TV, fireplace, computer monitors

Mid-Century Arty Chalet - 2 Min to Stratton Slopes

8.8 out of 10, Excellent, (3)
"The house is in a great location for skiing at Stratton! 5 mins drive to the base or shuttle service running every 30 mins. Perfect for a cozy ski weekend with the fireplace. We enjoyed it very much! "
Mid-Century Arty Chalet - 2 Min to Stratton Slopes
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, (23)
"A terrific place. Highly recommended. We had a great family ski vacation."
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults
MT SNOW | SKI BACK TRAIL | FREE SHUTTLE - Green Mountain House
Terrace/patio

MT SNOW | SKI BACK TRAIL | FREE SHUTTLE - Green Mountain House

10.0 out of 10, Exceptional, (15)
"Great location! Will be back!"
The price is AED 349
AED 1,253 total
includes taxes & fees
1 Apr - 2 Apr
MT SNOW | SKI BACK TRAIL | FREE SHUTTLE - Green Mountain House
Two Bedroom Chalet, Charming, Quiet, River Front
Interior

Two Bedroom Chalet, Charming, Quiet, River Front

9.4 out of 10, Exceptional, (74)
"Cindy was a pleasure to work with! Her home was exactly as described. We felt very comfortable in her home and the town of Jamaica is so cute! We went to the cutest little general store every morning to get breakfast and lunch. There are plenty of board games to enjoy waiting for you as you arrive… it is 15 minutes from Stratton Mountain. There is a foyer to leave your boots and jackets to hang. "
Two Bedroom Chalet, Charming, Quiet, River Front
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 AED 841
AED 2,044 total
includes taxes & fees
18 Mar - 19 Mar
Cozy Creekside Chalet centrally located near 4 ski resorts
The Snow Owl Chalet in Dover, Gorgeous 4-Bd 3-Bath - 10 Min. to Mount Snow!
Fridge, microwave, oven, stovetop

The Snow Owl Chalet in Dover, Gorgeous 4-Bd 3-Bath - 10 Min. to Mount Snow!

10.0 out of 10, Exceptional, (2)
"Last minute booking and Jennifer was quick to communicate and take care to insure us a nice stay"
The price is AED 1,087
AED 2,108 total
includes taxes & fees
18 Mar - 19 Mar
The Snow Owl Chalet in Dover, Gorgeous 4-Bd 3-Bath - 10 Min. to Mount Snow!
1 Mile To Ski at Mt Snow, FirePit, Hot Tub, Theater & Game Rooms, Moover stop
Outdoor dining

1 Mile To Ski at Mt Snow, FirePit, Hot Tub, Theater & Game Rooms, Moover stop

10.0 out of 10, Exceptional, (3)
"The house was great for our family of 5 and our dog. Located so close to Mt. Snow, it was an easy drive, clean and had anything we needed to cook and relax. The hosts are very communicative!"
The price is AED 1,128
AED 3,030 total
includes taxes & fees
30 Mar - 31 Mar
1 Mile To Ski at Mt Snow, FirePit, Hot Tub, Theater & Game Rooms, Moover stop
Ski chalet near Wilmington and beautiful Mt. Snow.
Dining

Ski chalet near Wilmington and beautiful Mt. Snow.

10.0 out of 10, Exceptional, (23)
"Great place, close to everything, all amenities and most importantly great hosts!"
Ski chalet near Wilmington and beautiful Mt. Snow.
Newly Renovated Rustic style home w/luxury bathrooms & mountain views, Sereni
Interior

Newly Renovated Rustic style home w/luxury bathrooms & mountain views, Sereni

9.8 out of 10, Exceptional, (58)
"Property was just as desribed in listing, clean, spacious and great for mulitple families and large groups. Julie was very resposive and accomodating to our every request. Heat and hot water was more than adequate even in below freezeing tempratures, although some extra blankets would have been appreciated.Property is very secluded, no cellular service as soon as you turn off the main roads - make sure GPS is set in advance. AWD vehicle is highly recommended during winter months.Would definitly...
Newly Renovated Rustic style home w/luxury bathrooms & mountain views, Sereni
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Terrace/patio

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

10.0 out of 10, Exceptional, (4)
"Clean, great location. Pet friendly and well thought out. "
The price is AED 514
AED 1,407 total
includes taxes & fees
1 Apr - 2 Apr
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
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
Classic Alpine Vermont Chalet
Fridge, microwave, oven, stovetop

Classic Alpine Vermont Chalet

10.0 out of 10, Exceptional, (10)
"The house was just what we needed for a family wedding in Manchester. Quite literally right off the highway but the house itself is nestled back and quiet so you don’t even hear the road. "
Classic Alpine Vermont Chalet
8 minutes to ski Mount Snow, Dog Friendly, Fire Pit, Hot Tub, Game Room, Private
Outdoor spa tub

8 minutes to ski Mount Snow, Dog Friendly, Fire Pit, Hot Tub, Game Room, Private

10.0 out of 10, Exceptional, (17)
"great space for adults and teenagers. loved the hot tub! "
8 minutes to ski Mount Snow, Dog Friendly, Fire Pit, Hot Tub, Game Room, Private
Dog Friendly Chalet in the Woods w/ Pool, Mt. Snow, VT
Exterior

Dog Friendly Chalet in the Woods w/ Pool, Mt. Snow, VT

9.8 out of 10, Exceptional, (7)
"The house was clean, spacious, and we’ll set up for ski groups. We used the pool and the club house. Plowing was prompt even with a big snow storm. "
Dog Friendly Chalet in the Woods w/ Pool, Mt. Snow, VT
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 Windham

Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.
Smart TV, fireplace, foosball, table tennis

Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.

10.0 out of 10, Exceptional, (47)
"We had a great stay at this property and every year a few families get together to spend a few days skiing and other winter activities. The house was a great layout for our group with plenty of spaces for all to sleep. Kids loved the downstairs while the adults love the game house. The property was well stocked with all needs if you forgot anything to make meal times easy. Host was great and if we had any questions they were answered right away. "
Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.
Long Trail House at Stratton Mountain Resort
Condo, 2 Bedrooms | Pool | Outdoor pool, open 10:00 AM to 10:00 PM, sun loungers

Long Trail House at Stratton Mountain Resort

3.0 star property
8.6 out of 10, Excellent, (74)
"Condo was great, cozy, and clean. Has access to the pool and hot tubs from back porch and has great Mountain View’s. The village had plenty of food, little expensive, but pretty good. Overall great place to stay and enjoy the mountain. "
The price is AED 1,267
AED 1,575 total
includes taxes & fees
13 Apr - 14 Apr
Long Trail House at Stratton Mountain Resort
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Property grounds

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

9.0 out of 10, Wonderful, (68)
"Was supposed to be first floor but had to go up lots of stairs. The place was very clean but dated. Better for young people not good for old people."
The price is AED 309
AED 1,005 total
includes taxes & fees
3 Apr - 4 Apr
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
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.