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Vacation Homes in Windham County

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12 Dec - 14 Dec
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19 Dec - 21 Dec
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2 Jan - 4 Jan
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30 Jan - 1 Feb

Top Cities in Windham County

We were pretty impressed with this. Never seen a frozen body of water strong enough for all of this activity!
Vacation HomesVacation Homes

Brattleboro

Brattleboro

Vacation Homes in Windham County

Interior
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

Vacation Home in Wilmington

10.0 out of 10, Exceptional, (227)
"Spectacular view and very peaceful."
United States
Beth B.
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
Fridge, microwave, oven, stovetop
500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

Vacation Home in Dover

9.8 out of 10, Exceptional, (48)
"Overall a nice stay, thanks Jen!"
United States
Anonymous traveler
500ft across the street to Carnitha. Gromet to main lift or take Moover to Base
Terrace/patio
Ski in Ski out Condo! Pool access

Vacation Home in Stratton

8.8 out of 10, Excellent, (3)
"Great location with plenty of space for the whole family. Highly recommend!"
United States
Joseph S.
The price is SAR 731
SAR 2,038 total
includes taxes & fees
9 Dec - 10 Dec
Ski in Ski out Condo! Pool access
Smart TV, fireplace, DVD player, table tennis
Beautiful Custom Built Timber Frame Home, Sleeps 11

Vacation Home in Wilmington

10.0 out of 10, Exceptional, (108)
"Met family here and was a fantastic place for get together "
United States
Melissa C.
Beautiful Custom Built Timber Frame Home, Sleeps 11
Fridge, microwave, oven, stovetop
Luxury Renovated Mount Snow Chalet with Upscale Amenities– Sleeps 12!

Vacation Home in West Dover Vermont

9.6 out of 10, Exceptional, (26)
"Perfect location to walk to slopes. The host was phenomenal! Very responsive and helpful. Can’t wait to stay again soon!"
United States
R B.
Luxury Renovated Mount Snow Chalet with Upscale Amenities– Sleeps 12!
Fridge, microwave, oven, stovetop
Spacious Riverfront Home 7 Minutes to Stratton!

Vacation Home in Jamaica

10.0 out of 10, Exceptional, (36)
"Perfect house for a few families to gather and have fun. "
United States
James D.
Spacious Riverfront Home 7 Minutes to Stratton!
Terrace/patio
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC

Vacation Home in Townshend

10.0 out of 10, Exceptional, (7)
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC
Interior
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Vacation Home in Dover

10.0 out of 10, Exceptional, (11)
"Beautiful new home, great for big family and friend groups. Comfortable bedding and furniture. Lots of open space and seating "
United States
Gena L.
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
TV, fireplace
Beautiful dog-friendly house w/ fireplace, firepit, bbq, deck, patio, w/d, wifi

Vacation Home in Mountain Acres

9.6 out of 10, Exceptional, (4)
"We had an amazing time in Vermont and really enjoyed our stay. All of the bathrooms are updated and the home is clean and big. Rooms are separated giving privacy throughout. Thank you!!"
United States
Anonymous traveler
Beautiful dog-friendly house w/ fireplace, firepit, bbq, deck, patio, w/d, wifi
Property grounds
Extraordinary Stratton Ski On/Ski Off Home

Vacation Home in Stratton

10.0 out of 10, Exceptional, (27)
"Wonderful host. Condo was well stocked with almost anything we needed. Lots of board games. "
United States
Reed T.
Extraordinary Stratton Ski On/Ski Off Home
Interior
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

Vacation Home in Whitingham

10.0 out of 10, Exceptional, (50)
"Great stay perfect for 2 people, relax on then porch and look at the lake! "
United States
Keith D.
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Interior
Stratton; Ski on/off, hot tub, King beds, 2 FPs, Office, Foosball

Vacation Home in Stratton

Stratton; Ski on/off, hot tub, King beds, 2 FPs, Office, Foosball
Outdoor dining
Six Bedroom Mountain Estate with Internet Access

Vacation Home in West Dover

10.0 out of 10, Exceptional, (16)
"This house was great for a family gathering! It had a lot of space, has a great game room for the kids, is very clean and comfortable, and is close to Mt. Snow! It checked off all the boxes we were looking for-"
United States
Steven Z.
Six Bedroom Mountain Estate with Internet Access
Terrace/patio
Bears Den Chalet | Ski Home Trail, Moover Shuttle, Outdoor Hot Tub!

Vacation Home in West Dover

10.0 out of 10, Exceptional, (14)
"The house is located conveniently close to everything you need to enjoy the mountain and surrounding amenities. Perfectly laid out home to enjoy apres ski with family and friends."
United States
Robert C.
Bears Den Chalet | Ski Home Trail, Moover Shuttle, Outdoor Hot Tub!
TV, fireplace
Pet Friendly Ski House, Game Rm, 4 Mins to Mt Snow

Vacation Home in Dover

2.0 star property
9.0 out of 10, Wonderful, (2)
"Weekend stay.Clean, comfortable, well equipped. Was as advertised.I would stay there again"
United States
Noah K.
The price is SAR 1,250
SAR 2,725 total
includes taxes & fees
5 Jan - 6 January 2026
Pet Friendly Ski House, Game Rm, 4 Mins to Mt Snow
Interior
Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes

Vacation Home in West Wardsboro

9.8 out of 10, Exceptional, (25)
"Enjoyed our time together at this home and in this area of Vermont."
United States
Patricia C.
Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes
Smart TV, fireplace
Spyglass village- Golf & Ski

Vacation Home in Wilmington

10.0 out of 10, Exceptional, (3)
"Great location, close to Mount Snow, ideal for skiing. Property is newly renovated, very functional and well appointed. We really enjoyed our stay."
United States
Emmanouhl T.
Spyglass village- Golf & Ski
Interior
Modern Mount Snow Gnarvana - Walk to Lodge & Lifts, Balcony, Loft

Vacation Home in Dover

10.0 out of 10, Exceptional, (20)
"Super nice place (very clean and modern) in a quiet area."
United States
Pete N.
The price is SAR 942
SAR 2,159 total
includes taxes & fees
7 Dec - 8 Dec
Modern Mount Snow Gnarvana - Walk to Lodge & Lifts, Balcony, Loft
Property grounds
Chimney Hill Charmer for Four Seasons of Fun!

Vacation Home in Wilmington

Chimney Hill Charmer for Four Seasons of Fun!
Fridge, microwave, oven, stovetop
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Vacation Home in Dover

10.0 out of 10, Exceptional, (8)
"Nice in all respects,"
United States
Ken
The price is SAR 1,672
SAR 3,925 total
includes taxes & fees
7 Dec - 8 Dec
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
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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Top Windham County Hotel Reviews

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent
"The staff are amazing! So friendly and welcoming. The lodge is so cute! The rooms were spotless and the hottub sparkling clean. The shuttle service until 10 pm was fantastic and the shuttle driver was very nice. We can't wait to visit again! "
Barbara 1-night trip
Posted 1 day ago
The Black Bear Lodge at Stratton Mountain Resort