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

Property grounds
Beautiful, private log cabin with huge, relaxing screened porch
10.0 out of 10, Exceptional, (24)
"The house was very comfortable for our family. It was well-stocked with plates, pots, and pans. Bed were comfortable."
Beautiful, private log cabin with huge, relaxing screened porch
Property grounds
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
10.0 out of 10, Exceptional, (183)
"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!"
The price is $476
$787 total
includes taxes & fees
May 20 - May 21
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
Terrace/patio
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!
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Fridge, microwave, oven, stovetop
Mt Snow, Summer house Escape- Spacious 4BR Cozy Home!
10.0 out of 10, Exceptional, (24)
"Such a cozy place to relax and spend time with family. My niece loved the selection of games. Very convenient location right in the middle of Dover."
Mt Snow, Summer house Escape- Spacious 4BR Cozy Home!
Fridge, microwave, stovetop, dishwasher
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!
Fridge, microwave, oven, stovetop
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
TV, fireplace
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!
View from property
Cool Barn reno with views. 5 mins to hike, restaurants, fishing...
10.0 out of 10, Exceptional, (50)
"Will be my first choice when I return to Manchester. Beautiful property, very comfortable layout and great privacy from main property. Thank you!"
Cool Barn reno with views. 5 mins to hike, restaurants, fishing...
Fridge, microwave, oven, stovetop
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
10.0 out of 10, Exceptional, (78)
"Stayed for a quick ski trip with our adult kids. House was a great location, very clean and comfortable. Wish we were there longer!!!"
The price is $175
$376 total
includes taxes & fees
Jun 2 - Jun 3
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Fridge, microwave, oven, stovetop
3-story dog-friendly home with private hot tub, firepit, grill, wood stove, EVC
10.0 out of 10, Exceptional, (2)
3-story dog-friendly home with private hot tub, firepit, grill, wood stove, EVC
Property grounds
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
Property grounds
By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.
9.8 out of 10, Exceptional, (57)
"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.
Property grounds
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.
TV, DVD player, books
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
Outdoor dining
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
Exterior
Summer Deals Free Gym Pool Pass- Luxury Log Home, 6 BR/4BA, Pool Table, Hot Tub
9.8 out of 10, Exceptional, (157)
"The place is beautiful and the stay was fantastic. It is up a couple mile hill/road from the center of town, just long enough to make you feel you are out of the hustle. The property presents very well. The rooms are large for private space with 2 common rooms that are just as large for group time. The one suggestion would be to add a check in book of information, including necessary passwords (WIFI) and local attractions/restaurants. We had much of this in the interaction with the host through...
Summer Deals Free Gym Pool Pass- Luxury Log Home, 6 BR/4BA, Pool Table, Hot Tub
Smart TV, books
Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton
9.8 out of 10, Exceptional, (28)
"Super clean and tidy. Good location with 5 nearby ski mountains. The listing does not state that the indoor fireplace can not be used; so we were disappointed to discover that on arrival."
The price is $399
$1,101 total
includes taxes & fees
May 16 - May 17
Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton
Exterior
Beautifully Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
9.8 out of 10, Exceptional, (75)
"A friend and I took our 11-year-old sons away for a ski weekend. This place was perfect. Close to the mountain and a short walk to town. Very comfortable, and frictionless."
The price is $139
$332 total
includes taxes & fees
Jun 3 - Jun 4
Beautifully Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Fridge, microwave, oven, stovetop
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
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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

Interior
Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.
10.0 out of 10, Exceptional, (29)
"We had a wonderful stay. The house has everything you need!"
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, (174)
"It was very clean and area is beautiful. The pictures did not show inside stairs and i just had back surgery. It was very difficult for me on stairs. I wish i knew that before booking.. Also the couch in living room was terrible to sit in. If they remodeled the upstairs, i would stay again. Thank you"
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Exterior
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
9.6 out of 10, Exceptional, (177)
"Third time as good as the first. We will return next year"
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.