Vacation Homes in Windham County

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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Windham County holiday homes

Outdoor dining

The Jelly Mill-A Peaceful River Retreat

The Jelly Mill-A Peaceful River Retreat
Guilford
10.0 out of 10, Exceptional, (67 reviews)
"Very cozy stay"
United States
Jayvonte M.
The Jelly Mill-A Peaceful River Retreat
Dining

Starry Skies: 7min to SkiStratton+PikesFalls+DogOK

Starry Skies: 7min to SkiStratton+PikesFalls+DogOK
Pikes Falls
9.4 out of 10, Exceptional, (17 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
TV, fireplace

Potter's Place | House in Jamaica with mountain views

Potter's Place | House in Jamaica with mountain views
East Jamaica
9.4 out of 10, Exceptional, (12 reviews)
"Very nice cabin,clean, well equipped with lots of little extras. Very quiet and pretty setting. Will definitely be back."
United States
Susan C.
Potter's Place | House in Jamaica with mountain views
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
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, (24 reviews)
"Beautiful property! Todd was responsive and an excellent host. Looking forward to staying again."
United States
Robert I.
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
Interior

Beautiful Custom Built Timber Frame Home, Sleeps 11

Beautiful Custom Built Timber Frame Home, Sleeps 11
Wilmington
10.0 out of 10, Exceptional, (116 reviews)
"House is beautiful …all wonderful !"
United States
Elizabeth
Beautiful Custom Built Timber Frame Home, Sleeps 11
Interior

Cozy cottage tucked away in the woods

Cozy cottage tucked away in the woods
Townshend
9.8 out of 10, Exceptional, (55 reviews)
"This is our second stay at the cozy cottage. It had everything to accommodate us and our dogs. It is super clean and everything we needed was provided. The hosts are wonderful and were able to get us in a little early so we would not be driving in the big snow storm. We appreciate their hospitality so much! "
United States
Stephanie L.
Cozy cottage tucked away in the woods
Terrace/patio

Beautiful 4 BR Townhome minutes from Mt Snow

Beautiful 4 BR Townhome minutes from Mt Snow
West Dover
10.0 out of 10, Exceptional, (36 reviews)
"The house had everything we could possibly need and perfect for 2 families enjoying a long weekend of skiing!"
United States
tim q.
Beautiful 4 BR Townhome minutes from Mt Snow
Property grounds

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
Property grounds

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
TV, fireplace

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
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
Smart TV, fireplace, table football, ping pong

Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna

Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna
Windham
10.0 out of 10, Exceptional, (57 reviews)
"Consistently great time at this place (3rd time there)"
United States
Chad B.
Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna
Interior

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.
Indoor pool, a heated pool

Everything you need - swim, relax, play outside!

Everything you need - swim, relax, play outside!
Londonderry
9.6 out of 10, Exceptional, (56 reviews)
"Wonderful house to stay at- the kids loved the pool! "
United States
Lily M.
Everything you need - swim, relax, play outside!
Outdoor dining

500 acre historic property w/private fishing lake, skiing + all-season fun

500 acre historic property w/private fishing lake, skiing + all-season fun
Londonderry
9.2 out of 10, Wonderful, (45 reviews)
"Place was perfect for a large crowd. The toy area was a huge hit with our grandson. "
United States
Beth B.
500 acre historic property w/private fishing lake, skiing + all-season fun
TV, fireplace

The Cardinal Lodge- A Riverside Retreat

The Cardinal Lodge- A Riverside Retreat
Newfane
The Cardinal Lodge- A Riverside Retreat
Smart TV, fireplace, video games, DVD player

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

Walk To Town, Hottub, Firepit, Games, Mt Snow
Wilmington
10.0 out of 10, Exceptional, (59 reviews)
"Great house loved the game room."
United States
Adam B.
The price is HK$1,959
HK$5,463 total
includes taxes & fees
26 May - 27 May
Walk To Town, Hottub, Firepit, Games, Mt Snow
TV, fireplace, DVD player, video library

Two-story, dog-friendly house

Two-story, dog-friendly house
Wardsboro
8.4 out of 10, Very good, (32 reviews)
"House was awesome! Fit a large group well! Would recommend for sure!"
United States
Maxwell P.
Two-story, dog-friendly house
Smart TV, fireplace, DVD player, table football

Spacious Vacation home in Chimney Hill near Mt Snow

Spacious Vacation home in Chimney Hill near Mt Snow
Wilmington
10.0 out of 10, Exceptional, (20 reviews)
"Amazing home. The perfect space for a fun family weekend. Cant wait to go back! "
United States
Katrina S.
Spacious Vacation home in Chimney Hill near Mt Snow
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

Latchis Hotel

Latchis Hotel

10/10 Excellent
"The staff was great very helpful!!! Very understanding and had patience with me. Thanks Peace&patience JRC"
John 1-night trip
Posted 3 hours ago
Latchis Hotel

Find out more about Windham County

Windham County Vacation Homes information

Number of reviews
568
Accommodation
430 Vacation Homes
Lowest Price
HK$5,463
Highest Price
HK$5,463

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