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Compare 106 Chalets in Windham with updated reviews, rates, and availability.

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

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

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 477
AED 1,349 total
includes taxes & fees
8 Apr - 9 Apr
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

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

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...
The price is AED 1,322
AED 3,283 total
includes taxes & fees
2 Apr - 3 Apr
Sunny Stratton Mountain Retreat: 5BD Modern Oasis w/Hot Tub, Pond, & BBQ Deck

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

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

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

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

Summer Adventures Await -- Book now for the Horse Show & Explore Manchester

10.0 out of 10, Exceptional, (50)
"We enjoyed skylight lodge. We get together with family and friends each year to do an annual fundraising event. The house was perfect for our group. The big fireplace was a great way to relax after a day of skiing or snowshoeing. "
Summer Adventures Await -- Book now for the Horse Show & Explore Manchester

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.

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,

Hot Tub, Theater & Game Rooms, Fire Pit, 1 mile to Mount Snow, nearby Moover bus

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 819
AED 2,714 total
includes taxes & fees
31 Mar - 1 Apr
Hot Tub, Theater & Game Rooms, Fire Pit, 1 mile to Mount Snow, nearby Moover bus

Expansive 7-BR Chalet 5-min from Mt. Snow

10.0 out of 10, Exceptional, (3)
"House is great, we had a large group. 2 living rooms, one with tv one without was a nice separation. To give some details on the layout, the bunk bed rm and twin room are off the living room on the main level, all other bd rooms are on the second floor. From the parking area to the main front door there are 31 steps.... not sure that was stated anywhere but hopefully everyone reads this review. I will stay here again if my group size demands it, it's close to mt snow, pretty secluded overall...
Expansive 7-BR Chalet 5-min from Mt. Snow

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

Stylish Mountain Getaway close to Stratton w/ Spa

9.8 out of 10, Exceptional, (7)
"Overall, a very good stay. The house is a bit smaller than we thought, but it was very clean and well stocked. The indoor fireplace and provided wood was a nice perk. The hot tub was not clean or well kept, so beware of that. There were body hairs and a brown scum ring around the edge."
Stylish Mountain Getaway close to Stratton w/ Spa

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

Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.

9.6 out of 10, Exceptional, (45)
"This is a beautiful property that is convenient to town. The only problem with this property is that there is a long term rental below this property that has a fairly large number of tenants who are at best inconsiderate, and at worst deliberately noisy. Expect doors being slammed hard enough to shake the entire unit at 3 AM and people arguing throughout the night. That is on a good night. If you can sleep through that noise this is the place for you. "
Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.

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

10.0 out of 10, Exceptional, (15)
"We had an amazing trip, and the host was very responsive and helpful with everything. The house was great, had everything we needed, and the private ski run back to the property was really fun. Highly recommend this property and the best host we have ever had!! Favoriting this place for a future stay!"
The price is AED 349
AED 1,262 total
includes taxes & fees
1 Apr - 2 Apr
MT SNOW | SKI BACK TRAIL | FREE SHUTTLE - Green Mountain House

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 2,049 total
includes taxes & fees
1 Apr - 2 Apr
Cozy Creekside Chalet centrally located near 4 ski resorts
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.

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

3.0 star property
8.6 out of 10, Excellent, (74)
"Nice, clean room in prime location"
The price is AED 1,267
AED 1,575 total
includes taxes & fees
13 Apr - 14 Apr
Long Trail House at Stratton Mountain Resort

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

9.6 out of 10, Exceptional, (211)
"Very cute cabin with fireplace and jacuzzi. Host provided firewood - which was a nice touch. Cabin is on dead end private road so, as mentioned, very peaceful. Lots of snow so no deck access, but imagine it would be great in summer too."
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
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.