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

Cottages in Windham County

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Check prices for these dates

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

Our top choices for Windham County cottages

A wooden deck with outdoor furniture, a white railing, and a view of a forest.

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!
A covered porch with white railings and two rocking chairs.

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
A covered outdoor seating area with two chairs and a table, overlooking a snowy forest.

3. 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
A wooden deck leading to a house with a view of a road and greenery.

4. 3 Mi to Mount Snow: Spacious West Dover Home

3 Mi to Mount Snow: Spacious West Dover Home
3.0 star property
West Dover
The price is Rp6.723.340
Rp11.562.199 total
includes taxes & fees
1 Sept - 2 Sept
3 Mi to Mount Snow: Spacious West Dover Home
A red building with a green roof, white porch, and a sign that reads "Studio."

5. 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!
A wooden cabin interior with a wooden ceiling, a fireplace, a sofa, a coffee table, and a dining area.

6. Londonderry Chalet w/ Deck, Fire Pit & Views!

Londonderry Chalet w/ Deck, Fire Pit & Views!
3.0 star property
Londonderry
Londonderry Chalet w/ Deck, Fire Pit & Views!
A two-story house with a covered patio, a separate garage, and a well-maintained lawn.

7. 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
A covered porch with wooden flooring, two green folding chairs, a wooden table, and a ceiling fan.

8. 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
A wooden deck with a table, chairs, and a bench.

9. Honey Paws Inn: Wilmington Home 6 Mi to Mount Snow

Honey Paws Inn: Wilmington Home 6 Mi to Mount Snow
3.0 star property
Wilmington
Honey Paws Inn: Wilmington Home 6 Mi to Mount Snow
A wooden deck with a table and chairs, surrounded by trees with autumn foliage.

10. 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!
A single-story house with a front porch, a small deck, and a well-maintained lawn.

11. 'mount Pine' Winter Retreat Near the Green Mtns!

'mount Pine' Winter Retreat 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 Retreat Near the Green Mtns!
A stone patio with picnic tables and a barbecue grill in front of a white building with a red roof.

12. 'john's Farmhouse in Mount Snow' on 120 Acres!

'john's Farmhouse in Mount Snow' on 120 Acres!
3.0 star property
Jacksonville
10.0 out of 10, Exceptional, (1 review)
"Beautiful home. Great for a family get away. Hosts were top notch. I stay in rentals all the time for work and this was great. I will bring my grand kids next time. "
United States
Jeffrey
'john's Farmhouse in Mount Snow' on 120 Acres!
A wooden deck with a view of a green landscape.

13. Jacksonville Cabin w/ Wraparound Deck & Views

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

14. Fishing Pond + Pool! Resort Retreat in Wilmington

Fishing Pond + Pool! Resort Retreat in Wilmington
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (1 review)
"What a great property! The fire pit, the basement game room, the kitchen, and the common spaces are all excellent. The process of working through a secondary property management company was slightly cumbersome but once we had the guest contact, Stephanie was great."
United States
Marc
Fishing Pond + Pool! Resort Retreat in Wilmington
A house with a deck, surrounded by trees and a grassy slope.

15. 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!
A hot tub on a wooden deck with a view of trees and a snowy landscape.

16. 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
A wooden deck with a table and chairs, surrounded by a railing, overlooking a forested area.

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!
A deck with outdoor furniture, a grill, and propane tanks.

18. 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
A wooden cabin with a porch featuring two wooden chairs and a window.

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
A wooden deck with a metal railing overlooking a forested area.

20. 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 traveller
Wilmington Retreat Near Trails, Skiing & Festivals
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

Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"I really have no complaints whatsoever! I would’ve loved a pancake conveyor belt to go with the breakfast but the waffle irons did the trick just the same."
Lindsay 2-night trip
Posted 5 hours ago
Hampton Inn Brattleboro

Find out more about Windham County

Windham County Cottages information

Number of reviews
11
Accommodation
94 Cottages
Lowest Price
Rp11.562.199
Highest Price
Rp11.562.199