Vacation Homes in Windham County

Compare and save
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Top Cities in Windham County

Our top choices for Windham County vacation homes

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Whitingham
9.8 out of 10, Exceptional, (48 reviews)
"Home is lovely, fun bedroom themes."
United States
Kate H.
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Walk To Town, Hottub, Firepit, Games, Mt Snow

Walk To Town, Hottub, Firepit, Games, Mt Snow
Wilmington
10.0 out of 10, Exceptional, (56 reviews)
"We were a group of 11 and we had a great weekend. Comfortable to stay and plenty to do!"
United States
Olivia R.
Walk To Town, Hottub, Firepit, Games, Mt Snow

Starry Skies: 7min to SkiStratton+PikesFalls+DogOK

Starry Skies: 7min to SkiStratton+PikesFalls+DogOK
Pikes Falls
9.4 out of 10, Exceptional, (16 reviews)
"Host was very responsive even late into the night. Clean rooms and adequate everything; towels, blankets, paper towels, etc... home away from home. Clear instructions on arrival and check out. "
United States
kit chi
Starry Skies: 7min to SkiStratton+PikesFalls+DogOK

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
Wardsboro
9.4 out of 10, Exceptional, (30 reviews)
"We had a wonderful Christmas week at Northern Quarters with our extended family, ages 5 months to 89 years old. The host was very helpful and accessible. The surroundings were beautiful —especially loved the brook and woods lighted up at night. Beds were comfortable and the houses were equipped with everything we needed to pull off meals for a crowd. The separate houses were perfect for accommodating late nights and early risers. Loved our walks and cross country skiing through the woods. Mt...
United States
Marilyn R.
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

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, (23 reviews)
"Great place and Todd was responsive and easy to deal with. "
United States
Jay A.
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Beautiful Custom Built Timber Frame Home, Sleeps 11

Beautiful Custom Built Timber Frame Home, Sleeps 11
Wilmington
10.0 out of 10, Exceptional, (115 reviews)
"House is beautiful …all wonderful !"
United States
Elizabeth
Beautiful Custom Built Timber Frame Home, Sleeps 11

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, (28 reviews)
"Amazing place to stay with family!"
United States
Manisha P.
Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes

Black Bear Brook: Between Mt. Snow and Berkshire East. Minutes to lakes/hiking.

Black Bear Brook: Between Mt. Snow and Berkshire East. Minutes to lakes/hiking.
Whitingham
9.8 out of 10, Exceptional, (11 reviews)
"We had a great stay! Everything was easy and communication was clear!"
United States
JT P.
Black Bear Brook: Between Mt. Snow and Berkshire East. Minutes to lakes/hiking.

Extraordinary Stratton Ski On/Ski Off Home

Extraordinary Stratton Ski On/Ski Off Home
Stratton
10.0 out of 10, Exceptional, (32 reviews)
"Property is just as described, lovely. Janel was attentive. Would stay there again! Great place for family or group."
United States
Laura A.
Extraordinary Stratton Ski On/Ski Off Home

Woodsy Getaway! Shuttle or Ski-home from Mt. Snow

Woodsy Getaway! Shuttle or Ski-home from Mt. Snow
West Dover
10.0 out of 10, Exceptional, (4 reviews)
"Great location and easy access to Mt Snow! All the conveniences of home!"
United States
Tina K.
Woodsy Getaway! Shuttle or Ski-home from Mt. Snow

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Stratton
7.8 out of 10, Good, (56 reviews)
"Location was great, pool, hot tubs and sauna were great"
United States
Lin M.
The price is AED 298
AED 924 total
includes taxes & fees
7 Apr - 8 Apr
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Beautiful townhome in charming Stratton for your relaxing getaway.

Beautiful townhome in charming Stratton for your relaxing getaway.
Stratton
10.0 out of 10, Exceptional, (2 reviews)
"Host Val was very helpful and reachable at all times. Home was great for our families, we enjoyed our stay!!"
United States
Danielle S.
Beautiful townhome in charming Stratton for your relaxing getaway.

Quiet Country 2 Bedroom Home Near Bellows Falls & Walpole — Easy I-91 Access

Quiet Country 2 Bedroom Home Near Bellows Falls & Walpole — Easy I-91 Access
Westminster
10.0 out of 10, Exceptional, (2 reviews)
"Nice, clean home with everything you need. Great communication. Would definitely stay again. "
United States
tina w.
Quiet Country 2 Bedroom Home Near Bellows Falls & Walpole — Easy I-91 Access

Deerfield Retreat | Shuttle to Mt.Snow w/Fireplace

Deerfield Retreat | Shuttle to Mt.Snow w/Fireplace
Dover
10.0 out of 10, Exceptional, (2 reviews)
"Very clean, comfortable and close to the mountain. Thanks Greg!"
United States
Stephen S.
Deerfield Retreat | Shuttle to Mt.Snow w/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

Casa Azul: HotTub, FirePit, Games, Mt Snow 10 Min

Casa Azul: HotTub, FirePit, Games, Mt Snow 10 Min
Dover
Casa Azul: HotTub, FirePit, Games, Mt Snow 10 Min

Valley Trail Riverfront Townhouse with EV Charging 2 miles from Mount Snow

Valley Trail Riverfront Townhouse with EV Charging 2 miles from Mount Snow
Dover
10.0 out of 10, Exceptional, (7 reviews)
Valley Trail Riverfront Townhouse with EV Charging 2 miles from Mount Snow

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, (65 reviews)
"Another great summer vacation with family at this beautiful property! Have already booked for next year."
United States
Shirlee B.
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Two-story, dog-friendly house

Two-story, dog-friendly house
Wardsboro
8.4 out of 10, Very Good, (31 reviews)
"House was awesome! Fit a large group well! Would recommend for sure!"
United States
Maxwell P.
Two-story, dog-friendly house

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (59 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is AED 606
AED 1,131 total
includes taxes & fees
29 Mar - 30 Mar
Family Friendly Hilltop House In Putney Vermont
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Windham County Hotel Reviews