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

Cottages in Windham County

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Top Cities in Windham County

Our top choices for Windham County cottages

1. The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
Chester
10.0 out of 10, Exceptional, (27 reviews)
"Even prettier than pictured. Very comfortable and dog-friendly. We enjoyed staying here and liked how old-fashioned it was, while still being comfortable and easy to navigate."
United States
Katharine H.
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

2. Forest cottage near Lake Raponda with sunroom, gas fireplace and firepit

Forest cottage near Lake Raponda with sunroom, gas fireplace and firepit
Wilmington
8.6 out of 10, Excellent, (79 reviews)
"The place itself is hard to find but the host was super personable and answered immediately. Really cute cabin! Good for a few day stay."
United States
Arianna K.
Forest cottage near Lake Raponda with sunroom, gas fireplace and firepit

3. Rare new Home on Lake Whitingham. Semi-priv beach

Rare new Home on Lake Whitingham. Semi-priv beach
Wilmington
10.0 out of 10, Exceptional, (9 reviews)
"Clean, quiet and so very peaceful. Exactly what we needed. Thank you for the beautiful escape."
United States
Anonymous traveler
Rare new Home on Lake Whitingham. Semi-priv beach

4. Vermont Country Cottage (Near Village)

Vermont Country Cottage (Near Village)
Londonderry
9.4 out of 10, Exceptional, (14 reviews)
"Convenient location for the event and places we wanted to visit!"
United States
Joe A.
Vermont Country Cottage (Near Village)

5. 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!

6. 4 Mi to Lake Raponda! Secluded Family Cottage

4 Mi to Lake Raponda! Secluded Family Cottage
Brattleboro
4 Mi to Lake Raponda! Secluded Family Cottage

7. Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow

Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow
Newfane
9.6 out of 10, Exceptional, (76 reviews)
"Great location for exploring the area. The cabin is private, without feeling isolated, and had everything we needed to enjoy our 3-night stay."
United States
Ed E.
Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow

8. 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

9. Cottage-Swim-Brook on Property-Views-Firepit-Woodstove-7 min to Stratton-Dogs OK

Cottage-Swim-Brook on Property-Views-Firepit-Woodstove-7 min to Stratton-Dogs OK
Jamaica
10.0 out of 10, Exceptional, (4 reviews)
"Nice and cozy, just like the listing shows. Great host. "
United States
Kytalia B.
Cottage-Swim-Brook on Property-Views-Firepit-Woodstove-7 min to Stratton-Dogs OK

10. '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!

11. 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

12. 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

13. 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!

14. 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

15. 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

16. 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

17. 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!

18. 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

19. 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

20. 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
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

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