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Compare 739 Vacation Homes in Windham with updated reviews, rates, and availability.

Quaint mountain retreat with a gas fireplace, balcony, central AC - dog-friendly
9.2 out of 10, Wonderful, (15)
"Great location- 10-15min from Stratton, beautiful views, all the amenities. Awesome decor, will definitely be back!"
Quaint mountain retreat with a gas fireplace, balcony, central AC - dog-friendly
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
9.6 out of 10, Exceptional, (30)
"My family really enjoyed this Lake House. The beautiful views of the lake were breathtaking. The house had everything we needed for preparing meals. The kitchen was functional and generally well equipped. The beds in the house were particularly comfortable. We enjoyed early morning coffee on the deck with perfect views of the lake. The location was great. Lots of wonderful hiking trials in close proximity. My only suggestion to the owners is to give the house a good deep cleaning. Nonetheless,...
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Your Barn!
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
10.0 out of 10, Exceptional, (184)
"The barn was spacious and had everything we needed. The property is breathtaking, great location to the town, and Jeff was a great host. Our dogs were welcome, living their best life running around the property, and it was so special to see the mountains and just breathe in the air there. Would love to come back in the warmer weather!"
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
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View from deck
Idyllic Lakefront House Suited Two Families
9.8 out of 10, Exceptional, (142)
"Ursula was super helpful and the location is very charming. Perfect spot for us!"
The price is AED 859
AED 1,894 total
includes taxes & fees
22 Jun - 23 Jun
Idyllic Lakefront House Suited Two Families
Lakefront home with amazing views, fireplace, firepit, & gas grill
9.8 out of 10, Exceptional, (58)
"Awesome house. Great location. I would stay there again for sure!"
Lakefront home with amazing views, fireplace, firepit, & gas grill
Lake
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
9.8 out of 10, Exceptional, (187)
"We had a lovely stay, the kayaks and canoe were the feature of one afternoon and we greatly enjoyed paddling around Lake Pauline and checking out both dam areas. The house is very clean and well maintained, we fell in love with all the windows and light coming in the bedroom across from the bathroom. The quick walk to the sugar house was a feature for my kids, they also loved having the wii in their room and playing Mario kart with their aunt/uncle."
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Summer 2015
By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.
9.8 out of 10, Exceptional, (58)
"We loved our stay at the lodge. We had two couples and kids ranging in age from 2 to 12. We did lots of skiing at Bromley but loved having Manchester so close to explore. The pinball arcade was a great rainy day activity for kids! The house was amazing and bigger than we imagined, we were all extremely comfortable. The only thing to mention is the stairs and upstairs loft are a bit scary for little ones. We blocked them with a baby gate and didn’t let the two year old up there, but it was fine...
By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.
Exterior
Beautiful, private log cabin with huge, relaxing screened porch
10.0 out of 10, Exceptional, (25)
"We had a great stay at Labrador Lodge! The house was comfortable and cozy. The layout of the home worked perfectly for our family and we loved being together on the quiet mountain road. The beautiful, large screen porch was our favorite part!"
Beautiful, private log cabin with huge, relaxing screened porch
Backyard view of home
Beautiful Custom Built Timber Frame Home, Sleeps 11
10.0 out of 10, Exceptional, (94)
"Great house and host. We enjoyed the great room and fireplace. Snow was an extra! Will definitely book again."
Beautiful Custom Built Timber Frame Home, Sleeps 11
Spacious home Featuring a hot tub, fire pit, fireplace and more!
9.0 out of 10, Wonderful, (4)
"We had a pleasant experience staying at this space for our gathering. It provided a quiet environment conducive to our needs. The host was very friendly and responsive, addressing any inquiries promptly. It's a peaceful and accommodating venue."
The price is AED 1,401
AED 3,584 total
includes taxes & fees
30 May - 31 May
Spacious home Featuring a hot tub, fire pit, fireplace and more!
Firepit and big lawn at The Reunion House
Perfect Reunion House w/fireplace & piano. Dogs welcome. Discounted ski tix at Bromley. Add private indoor pool on request.
9.8 out of 10, Exceptional, (22)
"Friendly host, ans check in process was very simple. House was big enough for 8 adults and 6 children. Location is 30-40 mins away from stratton, which we decided to go fo skiing. It felt a little further away due to traffic and busy long weekend."
Perfect Reunion House w/fireplace & piano. Dogs welcome. Discounted ski tix at Bromley. Add private indoor pool on request.
Welcome to End of the Road Stay! We are happy to host you!
Stay Safe! Stay strong!
10.0 out of 10, Exceptional, (39)
"Spacious and clean accommodation. Beds are comfy and lots of toys & games for the kids. We forgot that there is no real kitchen but it was clearly mentioned in the posting."
Stay Safe! Stay strong!
Stratton Vacation Rental | 4BR | 2BA | 2,000 Sq Ft | Stairs Required
Storybook Stratton House: 3 Mi to Mount Snow!
9.8 out of 10, Exceptional, (7)
"Overall the house was great. Exactly as advertised"
Storybook Stratton House: 3 Mi to Mount Snow!
Golf
Riverfront, family fun, amazing rec room, close to Magic & Okemo
9.8 out of 10, Exceptional, (7)
"Very comfortable and clean home. My friends and I came into town for a snowboarding trip, and the home was the perfect fit for us."
Riverfront, family fun, amazing rec room, close to Magic & Okemo
Winhall Vacation Rental | 4BR | 4BA | 4,121 Sq Ft | Stairs Required
Winhall Home w/ Deck + Views, 6 Mi to Ski Slopes!
10.0 out of 10, Exceptional, (2)
"My family loved staying at the Winhall property. The house was beautiful and extremely cozy. The guest contacts were accommodating and friendly. We are already planning our next trip!"
Winhall Home w/ Deck + Views, 6 Mi to Ski Slopes!
West Dover Vacation Rental | 5BR | 3BA | 3,365 Sq Ft | Stairs Required
West Dover Home w/ Deck, Grill & EV Outlet
9.8 out of 10, Exceptional, (16)
"Long weekend ski trip to Mt. Snow with three families. Layout of bedrooms and living spaces was perfect. Location to Mt. Snow and area market and restaurants was also perfect. We’ll be back."
West Dover Home w/ Deck, Grill & EV Outlet
Game room
5 miles to Stratton! Family-friendly with game room and deck!
9.0 out of 10, Wonderful, (2)
"This is an extremely well laid out house for a family to enjoy. There is plenty of spaces for everyone to spread out and find a nook to enjoy. And the fun old school video games made for great family fun. You are minutes from Stratton and yet you don't feel like you're bound to the ski world. They certainly put their attention on every detail---this is not a garage sale remodel."
The price is AED 1,837
AED 3,232 total
includes taxes & fees
3 Jun - 4 Jun
5 miles to Stratton! Family-friendly with game room and deck!
Three Bedroom home with loft
Three Bedroom home with loft
Home base at Mount Snow
10.0 out of 10, Exceptional, (5)
"Nice well maintained 70s style house, great location , highly recommend."
Home base at Mount Snow
Dover Vacation Rental | 3BR | 2BA | 1,250 Sq Ft | Stairs to Access
Relaxing Mountain Refuge: 4 Miles to Mt Snow!
10.0 out of 10, Exceptional, (6)
"This unit was so clean and well cared for. We felt right at home! And so close to both Mt Snow and all of the restaurants in Wilmington. We really enjoyed our stay and plan to return again."
Relaxing Mountain Refuge: 4 Miles to Mt Snow!
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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.

Other property types in Windham

Exterior
Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.
10.0 out of 10, Exceptional, (30)
"Awesome home on a beautiful piece of land. Suki was a great host and the house was well stocked with everything we needed!"
Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.
Exterior
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
9.8 out of 10, Exceptional, (175)
"This was a great stay- thank you so much! The property was clean and serene, the house adorable and cozy and the hot tub is always a plus! It was a great area, we’ll have to visit again sometime :)"
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
9.4 out of 10, Exceptional, (47)
"We loved our stay at the chalet. It's perfectly situated in the cutest little neighborhood, while also feeling very secluded. The chalet had everything we needed for our stay. While visiting we walked a few of the trails nearby, part of the Valley Trail and the Hoot, Toot and Whistle. They were both perfect for our pups, especially during hunting season. We gave our pups an extra squeeze in honor of Scarlet. Thank you for sharing your place with us! We would love to stay again!!"
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
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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