A wooden covered bridge over a river with stone walls on either side.

Vacation Homes in Windham County

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Check prices for these dates

In two weeks
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Top Cities in Windham County

A rural landscape with rolling hills, a winding road, and autumn-colored trees.
Vacation HomesVacation Homes

Whitingham

Whitingham

Our top choices for Windham County vacation homes

Dining

1. Starry Skies: 7min to SkiStratton+PikesFalls+DogOK

Starry Skies: 7min to SkiStratton+PikesFalls+DogOK
Pikes Falls
9.4 out of 10, Exceptional, (17 reviews)
"Great! "
United States
Christina P.
Starry Skies: 7min to SkiStratton+PikesFalls+DogOK
Property grounds

2. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (63 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is AED 585
AED 1,104 total
includes taxes & fees
1 Sep - 2 Sep
Family Friendly Hilltop House In Putney Vermont
TV, fireplace, books

3. Bright three-level home with water views, jetted tub, firepit, and pool table

Bright three-level home with water views, jetted tub, firepit, and pool table
Jacksonville
8.6 out of 10, Excellent, (38 reviews)
"House was perfect for our ski trip. Kids loved the loft bedroom and the house was warm and cozy. "
United States
Brian E.
Bright three-level home with water views, jetted tub, firepit, and pool table
Coffee/tea maker, fridge, microwave, stovetop

4. West Dover Home - 3 Miles to Mount Snow Resort!

West Dover Home - 3 Miles to Mount Snow Resort!
West Dover
9.2 out of 10, Wonderful, (28 reviews)
"This was a great find! The space was great for my big family (17 of us). It was clean, had more than enough bedrooms and bathrooms so everyone was comfortable. The host was very communicative and helped when needed. The weather wasn’t the greatest so we couldn’t take full advantage of the back yard, but the patio space was great."
United States
Lisette B.
West Dover Home - 3 Miles to Mount Snow Resort!
Indoor pool, a heated pool

5. SPLISH SPLASH! Explore Vermont!

SPLISH SPLASH! Explore Vermont!
Londonderry
9.6 out of 10, Exceptional, (57 reviews)
"Wonderful house to stay at- the kids loved the pool! "
United States
Lily M.
SPLISH SPLASH! Explore Vermont!
Property grounds

6. Red Brick Retreat - 8br 6ba Hot Tub Sauna Home Gym

Red Brick Retreat - 8br 6ba Hot Tub Sauna Home Gym
Londonderry
10.0 out of 10, Exceptional, (46 reviews)
"See above"
United States
Anonymous traveler
Red Brick Retreat - 8br 6ba Hot Tub Sauna Home Gym
Outdoor spa tub

7. Spacious Riverfront Home 7 Minutes to Stratton!

Spacious Riverfront Home 7 Minutes to Stratton!
Jamaica
10.0 out of 10, Exceptional, (44 reviews)
"Excellent stay with plenty of room for a group of ten."
United States
Eric P.
Spacious Riverfront Home 7 Minutes to Stratton!
Terrace/patio

8. Beautiful 4 BR Townhome minutes from Mt Snow

Beautiful 4 BR Townhome minutes from Mt Snow
West Dover
10.0 out of 10, Exceptional, (37 reviews)
"Great location with a great view! House was perfect for our family weekend getaway! "
United States
Dave F.
Beautiful 4 BR Townhome minutes from Mt Snow
Smart TV, fireplace

9. 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
Property grounds

10. 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

11. 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
Exterior

12. South Londonderry Home, Walk to Magic Mtn Ski Area

South Londonderry Home, Walk to Magic Mtn Ski Area
S Londonderry
8.6 out of 10, Excellent, (13 reviews)
"Tough to get much closer to the mountain. Our family had a great weekend staying at "Magic Moments" and the location ensured we were on the slopes bright and early."
United States
Dean N.
South Londonderry Home, Walk to Magic Mtn Ski Area
Interior

13. Cozy Lakeside Tiny Home, kayaks included, fishing, hot tub, Near Skiing

Cozy Lakeside Tiny Home, kayaks included, fishing, hot tub, Near Skiing
Whitingham
9.8 out of 10, Exceptional, (53 reviews)
"Great stay perfect for 2 people, relax on then porch and look at the lake! "
United States
Keith D.
Cozy Lakeside Tiny Home, kayaks included, fishing, hot tub, Near Skiing
Desk, iron/ironing board, WiFi (free), bed sheets

14. 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
9.6 out of 10, Exceptional, (37 reviews)
"Great place! Great communication with the host. Definitely coming back."
United States
Robert T.
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
Outdoor dining

15. The Jelly Mill-A Peaceful River Retreat

The Jelly Mill-A Peaceful River Retreat
Guilford
10.0 out of 10, Exceptional, (73 reviews)
"This is our second time staying here and we look forward to staying here again next year! We love it! Very peaceful. Hosts are excellent."
United States
Georgene M.
The Jelly Mill-A Peaceful River Retreat
Smart TV

16. Outdoor Enthusiasts Paradise in Beautiful Vermont!

Outdoor Enthusiasts Paradise in Beautiful Vermont!
Wilmington
10.0 out of 10, Exceptional, (26 reviews)
"We loved our stay, thank you!!"
United States
Mark R.
Outdoor Enthusiasts Paradise in Beautiful Vermont!
Interior

17. Cozy cottage tucked away in the woods

Cozy cottage tucked away in the woods
Townshend
9.8 out of 10, Exceptional, (58 reviews)
"Everything you could possibly want for a get away. Beds were comfortable. Living quarters were more than expected. Having a fire in the fireplace was wonderful and homey. We so enjoyed our relax and recharge weekend there. Definitely planning on a return trip."
United States
Laura Ann G.
Cozy cottage tucked away in the woods
Outdoor pool

18. 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, (72 reviews)
"Excellent home, great location "
United States
Antoinette L.
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Outdoor dining

19. 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, (53 reviews)
"We had such a great stay at Beth’s home. It was such a cozy log cabin! Beth was an incredible too! We can’t wait to go back. "
United States
Tyla G.
Beautiful, private log cabin with huge, relaxing screened porch
Terrace/patio

20. Ski In / Ski Out 4BR / 3BA Private Hot Tub and shared pool

Ski In / Ski Out 4BR / 3BA Private Hot Tub and shared pool
Stratton
9.2 out of 10, Wonderful, (15 reviews)
"Had a great stay. Would visit again. "
United States
Michael R.
Ski In / Ski Out 4BR / 3BA Private Hot Tub and shared pool
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

8/10 Good
"The room was very clean and the staff was amazing but the proximity of the hotel makes it hard to sleep in the morning. It’s at a very busy intersection, and the train comes through and blasts its horn early in the morning.It is a great place to stay, but if you want to sleep in, it’s not the right place for you."
Michelle 2-night trip
Posted 5 hours ago
Latchis Hotel

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