Vacation Homes in Windham County

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Check prices for these dates

In two weeks
13 Feb - 15 Feb
In two months
27 Mar - 29 Mar
In three months
24 Apr - 26 Apr
In four months
22 May - 24 May

Top Cities in Windham County

Stratton Pond in Vermont; Shutterstock ID 64897450; Purchase Order: -
Vacation HomesVacation Homes

Stratton

Stratton

Our top choices for Windham County vacation homes

Interior

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

Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
Wilmington
10.0 out of 10, Exceptional, (230 reviews)
"Spectacular view and very peaceful."
United States
Beth B.
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
Smart TV, fireplace, video games, books

500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

500ft across the street to Carnitha. Gromet to main lift or take Moover to Base
Dover
10.0 out of 10, Exceptional, (52 reviews)
"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
Fridge, microwave, oven, stovetop

Ski in Ski out Condo! Pool access

Ski in Ski out Condo! Pool access
Stratton
9.2 out of 10, Wonderful, (7 reviews)
"Comfortable in every room. Location is fantastic. Thank you for a great trip."
United States
Jeffrey
The price is AED 1,003
AED 2,394 total
includes taxes & fees
2 Feb - 3 Feb
Ski in Ski out Condo! Pool access
Interior

Beautiful Custom Built Timber Frame Home, Sleeps 11

Beautiful Custom Built Timber Frame Home, Sleeps 11
Wilmington
10.0 out of 10, Exceptional, (110 reviews)
"We had an excellent stay. Clean rooms. Well stocked with all everything you need. "
United States
Thomas K.
Beautiful Custom Built Timber Frame Home, Sleeps 11
Spa

Luxury Renovated Mount Snow Chalet with Upscale Amenities– Sleeps 12!

Luxury Renovated Mount Snow Chalet with Upscale Amenities– Sleeps 12!
West Dover Vermont
9.6 out of 10, Exceptional, (28 reviews)
"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!
Outdoor spa tub

Spacious Riverfront Home 7 Minutes to Stratton!

Spacious Riverfront Home 7 Minutes to Stratton!
Jamaica
10.0 out of 10, Exceptional, (37 reviews)
"Had a great time in VT, a perfect place to relax and enjoy time with family."
United States
Sue T.
Spacious Riverfront Home 7 Minutes to Stratton!
Outdoor dining

Luxury prop, Stunning views, private setting,pet friendly, fire pit ,WIFI,AC,EV

Luxury prop, Stunning views, private setting,pet friendly, fire pit ,WIFI,AC,EV
Townshend
10.0 out of 10, Exceptional, (9 reviews)
"Had a great time . Excellent communication Very clean .Would definitely stay there again. "
United States
Chris R.
Luxury prop, Stunning views, private setting,pet friendly, fire pit ,WIFI,AC,EV
Interior

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

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
Dover
10.0 out of 10, Exceptional, (17 reviews)
"Beautiful house with everything we needed for a fun family vacation! The kids loved the bunk room. Todd was great to communicate with and made check in/check out super easy. Would stay again! "
United States
Jennifer O.
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

Beautiful dog-friendly house w/ fireplace, firepit, bbq, deck, patio, w/d, wifi
Mountain Acres
9.6 out of 10, Exceptional, (4 reviews)
"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

Extraordinary Stratton Ski On/Ski Off Home
Stratton
10.0 out of 10, Exceptional, (29 reviews)
"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

Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Whitingham
10.0 out of 10, Exceptional, (50 reviews)
"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
Outdoor spa tub

Stratton; Ski on/off, hot tub, King beds, 2 FPs, Office, Foosball

Stratton; Ski on/off, hot tub, King beds, 2 FPs, Office, Foosball
Stratton
Stratton; Ski on/off, hot tub, King beds, 2 FPs, Office, Foosball
Outdoor dining

Six Bedroom Mountain Estate with Internet Access

Six Bedroom Mountain Estate with Internet Access
West Dover
9.6 out of 10, Exceptional, (17 reviews)
"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!

Bears Den Chalet | Ski Home Trail, Moover Shuttle, Outdoor Hot Tub!
West Dover
10.0 out of 10, Exceptional, (18 reviews)
"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

Pet Friendly Ski House, Game Rm, 4 Mins to Mt Snow
Dover
9.4 out of 10, Exceptional, (3 reviews)
"Great home! The family room is just amazing. Kitchen has everything and makes Vermont travel easy. Can’t beat the location, either!"
United States
Maureen L.
Pet Friendly Ski House, Game Rm, 4 Mins to Mt Snow
Interior

Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes

Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes
West Wardsboro
9.8 out of 10, Exceptional, (26 reviews)
"Amazing place to stay with family!"
United States
Manisha P.
Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes
Smart TV, fireplace

Spyglass village- Golf & Ski

Spyglass village- Golf & Ski
Wilmington
10.0 out of 10, Exceptional, (3 reviews)
"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
Dining

Modern Mount Snow Gnarvana - Walk to Lodge & Lifts, Balcony, Loft

Modern Mount Snow Gnarvana - Walk to Lodge & Lifts, Balcony, Loft
Dover
10.0 out of 10, Exceptional, (23 reviews)
"Super nice place (very clean and modern) in a quiet area."
United States
Pete N.
The price is AED 1,154
AED 2,374 total
includes taxes & fees
1 Feb - 2 Feb
Modern Mount Snow Gnarvana - Walk to Lodge & Lifts, Balcony, Loft
Property grounds

Chimney Hill Charmer for Four Seasons of Fun!

Chimney Hill Charmer for Four Seasons of Fun!
Wilmington
10.0 out of 10, Exceptional, (3 reviews)
"The property was clean, well stocked and super pet friendly."
United States
Megan B.
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!!!

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Dover
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful neighborhood to take walks. Home was very clean, as you see in the photo. Very spacious and relaxing. Pretty home overall."
United States
Stephen G.
The price is AED 2,628
AED 5,344 total
includes taxes & fees
2 Feb - 3 Feb
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

Colonial Motel And Spa

Colonial Motel And Spa

10/10 Excellent
"Amenities were great!"
Adrienne 3-night trip
Posted 10 hours ago
Colonial Motel And Spa