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Compare 791 Vacation Homes in Windham with updated reviews, rates, and availability.

Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer

8.6 out of 10, Excellent, (4)
"Our group had a great time enjoying this bright open space. Such a pretty place. Michael was very responsive and communications were timely and simple. Nice place for gathering."
Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer

Beautiful! 5 Beds-5 baths Home, Spectacular Views of Stratton, On Shuttle

10.0 out of 10, Exceptional, (39)
"This property couldn’t be better situated or more accommodating in regards to size, layout and comfort. With 3 master suites and additional rooms for children our large family had plenty of space to spread out. The shuttle to and from the mountain are an added bonus to avoid the parking scene at the base of the mountain. We couldn’t have enjoyed our stay more, and will be back again! "
Beautiful! 5 Beds-5 baths Home, Spectacular Views of Stratton, On Shuttle

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

9.8 out of 10, Exceptional, (169)
"Great house for family. Enjoyed our trip. So close to Okemo. "
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

Secluded home with game room, private hot tub, golf, river & mtn views, firepit

9.8 out of 10, Exceptional, (6)
"Very nice. Could use curtains or blinds in more rooms."
Secluded home with game room, private hot tub, golf, river & mtn views, firepit

Idyllic Lakefront House Suited Two Families

9.6 out of 10, Exceptional, (157)
"We really enjoyed our stay at the lake house. We had great views of the lake and the kitchen was very well stocked. The beds were comfortable and the house was very clean and nicely decorated. Thank you for the incredible stay and we will be staying again!"
Idyllic Lakefront House Suited Two Families

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

10.0 out of 10, Exceptional, (6)
"Great house, great location, Great communication with Todd. Will be back for sure!!!! Thanks for everything Todd. "
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

7.0 out of 10, Good, (15)
"Great place. Clean and comfortable. Nicely stocked kitchen with newer appliances. Sauna was amazing. Had 10 inches of snow one morning and it was fully plowed by 7am!"
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

Bear Pass - Mountain View by RedAwning

10.0 out of 10, Exceptional, (1)
"Great house. 35 minutes from Stratton mountain. House had everything needed, plenty of supplies, towels, blankets, etc. highly recommended. Ad was exactly what you got"
The price is AED 871
AED 2,285 total
includes taxes & fees
7 Mar - 8 Mar
Bear Pass - Mountain View by RedAwning

3-story dog-friendly home with private hot tub, firepit, grill, wood stove, EVC

10.0 out of 10, Exceptional, (6)
"Our group of 10 stayed three nights for a family ski weekend. Check in and out was easy; house was clean and the layout worked well for two families; location was convenient. Highly recommended. "
3-story dog-friendly home with private hot tub, firepit, grill, wood stove, EVC

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

9.8 out of 10, Exceptional, (94)
"Everything was as advertised! Great location and easy to find. "
The price is AED 720
AED 1,510 total
includes taxes & fees
1 Apr - 2 Apr
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Ground-floor apartment with pool, hot tub, tennis & gym access - near skiing

8.8 out of 10, Excellent, (3)
"Close to skiing"
Ground-floor apartment with pool, hot tub, tennis & gym access - near skiing

7200 sf Villa & Barn on 4 Acre Manchester Estate

9.6 out of 10, Exceptional, (8)
"We were absolutely delighted with our stay at the villa. The house is big, spacious, and most importantly, clean. The house has everything you need for a comfortable stay. Everything is thought out to the smallest detail. We had both kids and teenagers with us - everyone felt comfortable. Lots of space, a large table for a large company. The location is literally 3 minutes from the city center, where there are many shops and restaurants. 30 minutes from the ski resort. There were no problems...
7200 sf Villa & Barn on 4 Acre Manchester Estate

Dog-friendly house with picturesque mountain view & near skiing - close to Okemo

9.8 out of 10, Exceptional, (50)
"This is a lovely home -- spacious, beautifully furnished, and well-located, about 15 minutes from Okemo & downtown Ludlow. 4wd recommended for winter visitors: the house is up a steep hill, and in January the road surface was packed-down snow, so it was slippery for cars without all-wheel-drive."
Dog-friendly house with picturesque mountain view & near skiing - close to Okemo

Relaxing Retreat in the Heart of Dover

Relaxing Retreat in the Heart of Dover

Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Hike, Indoor Pool, Relax!

10.0 out of 10, Exceptional, (1)
"We had such a lovely time in this well loved cabin. Super quiet location and well stocked with everything we needed for our end of year ski trip in Stratton. The owner was very friendly and helpful. We hope we will be back soon!"
Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Hike, Indoor Pool, Relax!

NEW - Beautiful mountain home steps to Okemo, Great for Wedding stays

10.0 out of 10, Exceptional, (35)
"Property was super clean and SO CLOSE to the mountain. Everything was perfect- no complaints! "
NEW - Beautiful mountain home steps to Okemo, Great for Wedding stays

Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!

10.0 out of 10, Exceptional, (47)
"Condo was spacious and supplied with everything we needed for a great stay! We cooked 2 out of 3 nights so we appreciated that the kitchen was stocked with any spice you would need to prepare meals, not just the usual salt & pepper only. The location was perfect for our ski trip to Mount Snow and the market was also close by so once we were settled in there was very little driving to do. The living room furniture was comfy, and the dining area was huge and both had gorgeous views of the...
The price is AED 386
AED 1,295 total
includes taxes & fees
24 Mar - 25 Mar
Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!

Cozy retreat near slopes

5.0 out of 10, (8)
"Unit is a little outdated but nice.Not truly a ski in - out since you have to walk on the road about 200 yards to get to the Sachem trail.Condo does need ice cube trays since the ice maker is not working.Also the down stairs bath room heater does not work and would be nice since this is where the bath tub is located"
Cozy retreat near slopes

4 Season Secluded Lakefront Home near Ski Mountains

9.4 out of 10, Exceptional, (72)
"Overall a nice spot and great location for skiing and probably other activities. We were skiing.House is a bit rustic but very nice for what we were looking for and value for the money. Owner was very helpful and followed up after our stay. Would do it again and recommend."
4 Season Secluded Lakefront Home near Ski Mountains

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

9.6 out of 10, Exceptional, (36)
"The home is as described with plenty of space for my family of 5. The kitchen was well stocked, and the bathrooms were clean. Plenty of towels and the beds were firm with clean sheets. The views of Lake Rescue were beautiful. The driveway was snow-covered, but with a 4WD, you should have no issue. The 'commute' to Okemo was easy - 8min max. The house seems to have been empty, so a musty smell permeated the home for the first day until the air circulated a few times. Not a big deal. The gas...
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
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, (46)
"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
8.4 out of 10, Very Good, (73)
"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 1,341
AED 1,666 total
includes taxes & fees
1 Apr - 2 Apr
Long Trail House at Stratton Mountain Resort

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

9.2 out of 10, Wonderful, (67)
"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 367
AED 1,126 total
includes taxes & fees
9 Mar - 10 Mar
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.