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

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Top Cities in Windham County

A calm lake reflecting a forest with autumn foliage.
CottagesCottages

Brattleboro

Brattleboro

Our top choices for Windham County cottages

Exterior

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

The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
Chester
10.0 out of 10, Exceptional, (23 reviews)
"Beautiful location, nice yard, and very quiet. The home has real potential but needs some TLC to realize it."
United States
Anonymous traveller
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
House (Multiple Bedrooms) | Interior

2. 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!
Exterior

3. 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)
Exterior

4. Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Wilmington
8.6 out of 10, Excellent, (76 reviews)
"Absolutely charming cottage in a beautiful and convenient location. Nicely equipped with a dishwasher and washer and dryer. Elegant and updated bathrooms. The home was clean and very comfortable. The only negative was that the mattresses could be replaced."
United States
Bronwyn
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Exterior

5. 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, (8 reviews)
"Very nice place."
United States
michael r.
Rare new Home on Lake Whitingham. Semi-priv beach
Cottage (2 Bedrooms) | Interior

6. 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
House (4 Bedrooms) | Interior

7. 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 CA $530
CA $911 total
includes taxes & fees
Aug 16 - Aug 17
3 Mi to Mount Snow: Spacious West Dover Home
House (2 Bedrooms) | Interior

8. 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
Exterior

9. 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, (74 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
Exterior

10. 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
House (3 Bedrooms) | Interior

11. 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!
House (4 Bedrooms) | Interior

12. 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!
House (3 Bedrooms) | Front of property

13. 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
House (4 Bedrooms) | Interior

14. 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
House (1 Bedroom) | Front of property

15. 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!
House (3 Bedrooms) | Front of property

16. Jacksonville Cabin w/ Wraparound Deck & Views

Jacksonville Cabin w/ Wraparound Deck & Views
3.0 star property
Jacksonville
Jacksonville Cabin w/ Wraparound Deck & Views
House (3 Bedrooms) | Interior

17. '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!
House (3 Bedrooms) | Interior

18. 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!
House (4 Bedrooms) | Interior

19. 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
House (4 Bedrooms) | Interior

20. 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
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

Inn At Mount Snow

Inn At Mount Snow

10/10 Excellent
"This was such a delightful treat. The property is renovated and every room is beautifully decorated yet unique. The common areas are beautiful and offer every small detail you could want. From fresh cookies, s'mores kits, bonfire kits, board games and a record player with plenty of musical choices. This property offers free breakfast daily. The breakfast was delicious with fresh granola, muffins, cereal, fruit, and yogurt. The innkeepers are friendly and helpful. They live on the property and are available if you need anything. The views from the property are spectacular. I would highly recommend this property and look forward to staying here again."
Jeffrey 1-night trip
Posted less than an hour ago
Inn At Mount Snow

Find out more about Windham County

Windham County Cottages information

Number of reviews
131
Accommodation
102 Cottages
Lowest Price
CA $911
Highest Price
CA $911

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