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Vacation Homes in Windham County

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Top cities in Windham County

A snow-covered road winding through a forested area with buildings and mountains in the background.
Hotels

West Dover

West Dover

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Apartments
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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Windham County holiday homes

A living room with a stone fireplace, a flat-screen TV mounted above it, a sofa, and a sliding glass door leading to an outdoor patio.

1. 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, (62 reviews)
"Perfect location and nicely decorated and had a lot of amenities. "
United States
Cindy D.
500ft across the street to Carnitha. Gromet to main lift or take Moover to Base
A modern kitchen with a built-in fireplace, wine storage, and a dining area with wooden furniture.

2. 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, (14 reviews)
"great location easy access to the mountain and the pool was outstanding."
United States
jim f.
The price is HK$3,634
HK$8,376 total
includes taxes & fees
8 Nov - 9 Nov
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
A spacious living room with a fireplace, a dining area, and a kitchen with wooden cabinets and a microwave.

3. Book the Lemondrop for your Thanksgiving and experience Vermont’s Fall Magic

Book the Lemondrop for your Thanksgiving and experience Vermont’s Fall Magic
Dover
10.0 out of 10, Exceptional, (46 reviews)
"Lovely house - perfect for a ski trip!"
United States
Alexander H.
The price is HK$2,371
HK$4,690 total
includes taxes & fees
9 Nov - 10 Nov
Book the Lemondrop for your Thanksgiving and experience Vermont’s Fall Magic
A large, two-story house with a covered porch and string lights.

4. 5 Bdrm Lakehouse, sleeps 18, private dock, hot tub, 15 minutes to Mount Snow

5 Bdrm Lakehouse, sleeps 18, private dock, hot tub, 15 minutes to Mount Snow
Wilmington
9.8 out of 10, Exceptional, (109 reviews)
"Fantastic place!"
United States
Elizabeth C.
5 Bdrm Lakehouse, sleeps 18, private dock, hot tub, 15 minutes to Mount Snow
A wooden door leading to a deck with a view of a lake and mountains.

5. Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews

Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews
Wilmington
10.0 out of 10, Exceptional, (247 reviews)
"Great Lake view and amazing public beach at the end of the driveway."
United States
Brendan S.
Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews
A room with a stone fireplace, wooden beams, and large windows.

6. Beautiful Custom Built Timber Frame Home, Sleeps 11

Beautiful Custom Built Timber Frame Home, Sleeps 11
Wilmington
10.0 out of 10, Exceptional, (126 reviews)
"Wonderful stay!!"
United States
Alicia M.
Beautiful Custom Built Timber Frame Home, Sleeps 11
A pool area with a wooden deck, surrounded by a wooden fence, and a view of a forested landscape with hills in the background.

7. Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Townshend
10.0 out of 10, Exceptional, (78 reviews)
"Comfortable home for 11 of us with plenty of room to spread out… loved the screened porch and massive lawn with curving driveway. Wonderful visit for our three generation family reunion!"
United States
karen g.
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
A wooden staircase leading to a red house with the number 306 on the door.

8. The Jelly Mill-A Peaceful River Retreat

The Jelly Mill-A Peaceful River Retreat
Guilford
10.0 out of 10, Exceptional, (77 reviews)
"Very cozy stay"
United States
Jayvonte M.
The Jelly Mill-A Peaceful River Retreat
A covered wooden deck with wicker furniture and a glass table, overlooking a forested area.

9. Beautiful, private log cabin with huge, relaxing screened porch

Beautiful, private log cabin with huge, relaxing screened porch
Townshend
9.8 out of 10, Exceptional, (57 reviews)
"I love how spacious it is. We fit our party of nine perfectly!"
United States
Nina G.
Beautiful, private log cabin with huge, relaxing screened porch
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

10. Long Trail House 368 condo in Stratton Village, walk to the lifts

Long Trail House 368 condo in Stratton Village, walk to the lifts
Stratton
The price is HK$657
HK$1,994 total
includes taxes & fees
8 Nov - 9 Nov
Long Trail House 368 condo in Stratton Village, walk to the lifts
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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