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

Cottages in Windham County

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Our top choices for Windham County cottages

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

West Dover Home - 3 Miles to Mount Snow Resort!
3.0 star property
West Dover
10.0 out of 10, Exceptional, (1 review)
"Beautiful home, spacious, huge back yard. Close to everything you need. Hoping to return soon!!"
United States
Jacqueline
West Dover Home - 3 Miles to Mount Snow Resort!

2. 4 Mi to Lake Raponda! Secluded Family Cottage

4 Mi to Lake Raponda! Secluded Family Cottage
3.0 star property
Wilmington
4 Mi to Lake Raponda! Secluded Family Cottage

3. 'mount Pine' Winter Escape Near the Green Mtns!

'mount Pine' Winter Escape Near the Green Mtns!
3.0 star property
Wardsboro
10.0 out of 10, Exceptional, (1 review)
"Amazing place! Super clean and cozy, and host was extremely nice and communicative. Highly recommend."
United States
Alexander
'mount Pine' Winter Escape Near the Green Mtns!

4. Spacious Home,ppong,darts,pick Ball Net, 6mi mt sn

Spacious Home,ppong,darts,pick Ball Net, 6mi mt sn
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (2 reviews)
"This place was absolutely perfect, very clean and very well taken care of."
United States
Charles
Spacious Home,ppong,darts,pick Ball Net, 6mi mt sn

5. Spacious Vermont Farmhouse 3 Mi to Mount Snow

Spacious Vermont Farmhouse 3 Mi to Mount Snow
3.0 star property
West Dover
Spacious Vermont Farmhouse 3 Mi to Mount Snow

6. Wilmington Vacation Rental Near Hiking and Skiing!

Wilmington Vacation Rental Near Hiking and Skiing!
3.0 star property
Wilmington
Wilmington Vacation Rental Near Hiking and Skiing!

7. Cozy Mountain Retreat w/ Deck ~ 3 Mi to Mount Snow

Cozy Mountain Retreat w/ Deck ~ 3 Mi to Mount Snow
3.0 star property
West Dover
Cozy Mountain Retreat w/ Deck ~ 3 Mi to Mount Snow

8. 4 Mi to Stratton Mountain Resort! Cabin w/ Hot Tub

4 Mi to Stratton Mountain Resort! Cabin w/ Hot Tub
3.0 star property
Pikes Falls
4 Mi to Stratton Mountain Resort! Cabin w/ Hot Tub

9. Hiking Trails On-site: Cozy Falls Brook Cabin

Hiking Trails On-site: Cozy Falls Brook Cabin
3.0 star property
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"This is exactly how it’s described- perfect cozy spot- babbeling brook to keep you company while sitting on the porch - fire pit for cozy evenings and cabin inside is perfection- cozy cozy cozy!! Matt was the perfect host and readily available- hoping to return!! 15 mins from farmers markets, covered bridges, shops, food, drinks and entertainment ❤️"
United States
sarah
Hiking Trails On-site: Cozy Falls Brook Cabin

10. Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!

Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
3.0 star property
Vernon
10.0 out of 10, Exceptional, (1 review)
"We had a truly wonderful stay. The cottage and property are beautiful, peaceful and very special. Great views! Our host thought of everything, it's very comfortable and lovely. Best place to stay in Southern Vermont! Don't miss the Tiny Bread Box on Saturdays; it's just up the road. We'll defiantly be back for another visit."
United States
gloria
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!

11. Wilmington Retreat Near Trails, Skiing & Festivals

Wilmington Retreat Near Trails, Skiing & Festivals
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (2 reviews)
"Great location and awesome house. Owners were easy to communicate with. "
United States
Anonymous traveler
Wilmington Retreat Near Trails, Skiing & Festivals

12. 10 Mi to Mt Snow! Grand Estate Built to Entertain

10 Mi to Mt Snow! Grand Estate Built to Entertain
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (2 reviews)
"Wonderful home! Very comfortable and clean. Highly recommend. "
United States
Amanda
10 Mi to Mt Snow! Grand Estate Built to Entertain

13. Charming Putney Home: Porch, Grill & Hiking Trails

Charming Putney Home: Porch, Grill & Hiking Trails
3.0 star property
Putney
Charming Putney Home: Porch, Grill & Hiking Trails

14. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (1 review)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
United States
Mark
Charming Wilmington Cabin, 8 Mi. to Mt Snow!

15. West Dover Vacation Rental w/ Hot Tub Near Mt Snow

West Dover Vacation Rental w/ Hot Tub Near Mt Snow
3.0 star property
West Dover
West Dover Vacation Rental w/ Hot Tub Near Mt Snow

16. Luxe 5,000 Sq Ft Retreat: 5 Mi to Stratton Resort

Luxe 5,000 Sq Ft Retreat: 5 Mi to Stratton Resort
3.0 star property
Pikes Falls
Luxe 5,000 Sq Ft Retreat: 5 Mi to Stratton Resort

17. Home 15 Mi to Berkshire East & Mount Snow!

Home 15 Mi to Berkshire East & Mount Snow!
3.0 star property
Whitingham
10.0 out of 10, Exceptional, (1 review)
"Everything was absolutely amazing!!! This home was beautiful!!! The property was great too!! Host was amazing and kind and very good with communication!!! My family and I had an amazing time during our stay!!!"
United States
Kaylene
Home 15 Mi to Berkshire East & Mount Snow!

18. Wilmington Home on 18 Acres ~ 9 Mi to Skiing!

Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (1 review)
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!

19. 4 Mi to Mount Snow: West Dover Cabin w/ Game Room

4 Mi to Mount Snow: West Dover Cabin w/ Game Room
3.0 star property
West Dover
4 Mi to Mount Snow: West Dover Cabin w/ Game Room

20. Jacksonville Cabin w/ Wraparound Deck & Views

Jacksonville Cabin w/ Wraparound Deck & Views
3.0 star property
Jacksonville
Jacksonville Cabin w/ Wraparound Deck & Views
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

Find out more about Windham County

Windham County Cottages information

Number of reviews
11
Accommodation
95 Cottages
Lowest Price
Highest Price

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