Cottages in Windham County

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sep - 6 Sep

Our top choices for Windham County cottages

House (Multiple Bedrooms) | Interior

West Dover Home - 3 Miles to Mount Snow Resort!

West Dover Home - 3 Miles to Mount Snow Resort!
3.0 star property
West Dover
West Dover Home - 3 Miles to Mount Snow Resort!
House (3 Bedrooms) | Interior

Near Hiking & Skiing: Home in Wilmington!

Near Hiking & Skiing: Home in Wilmington!
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (1 review)
"Owner Brent was helpful and quick to respond to questions. The house is near Mount Snow great for skiing! Very nice place to stay, we will definitely stay again when booking for next year."
United States
Donna
Near Hiking & Skiing: Home in Wilmington!
House (1 Bedroom) | Front of property

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

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 (2 Bedrooms) | Interior

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
The price is 4.030.785 ₫
10.804.611 ₫ total
includes taxes & fees
15 Jun - 16 Jun
Hiking Trails On-site: Cozy Falls Brook Cabin
House (4 Bedrooms) | Interior

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!
Cottage (2 Bedrooms) | Interior

Rustic Marlboro Cottage: 4 Mi to Lake Raponda!

Rustic Marlboro Cottage: 4 Mi to Lake Raponda!
3.0 star property
Wilmington
Rustic Marlboro Cottage: 4 Mi to Lake Raponda!
House (4 Bedrooms) | Interior

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
House (5 Bedrooms) | Interior

'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!
House (3 Bedrooms) | Interior

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 (3 Bedrooms) | Interior

Cozy Log Cabin Near Mt Snow: Views, Modern Comfort

Cozy Log Cabin Near Mt Snow: Views, Modern Comfort
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (1 review)
Cozy Log Cabin Near Mt Snow: Views, Modern Comfort
House (3 Bedrooms) | Front of property

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

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 (3 Bedrooms) | Front of property

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!
House (3 Bedrooms) | Interior

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
House (3 Bedrooms) | Front of property

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

2 Mi to Golfing & Hiking: Spacious Wilmington Home

2 Mi to Golfing & Hiking: Spacious Wilmington Home
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
2 Mi to Golfing & Hiking: Spacious Wilmington Home
House (4 Bedrooms) | Front of property

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
House (4 Bedrooms) | Interior

Home 15 Mi to Berkshire East & Mount Snow!

Home 15 Mi to Berkshire East & Mount Snow!
3.0 star property
Whitingham
Home 15 Mi to Berkshire East & Mount Snow!
House (4 Bedrooms) | Interior

Golf, Hike & Unwind: Spacious Dover Retreat!

Golf, Hike & Unwind: Spacious Dover Retreat!
3.0 star property
West Dover
Golf, Hike & Unwind: Spacious Dover Retreat!
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
"It was fine, no complaints, as advertised and expected."
Nicole 1-night trip
Posted 9 hours ago
Hampton Inn Brattleboro

Find out more about Windham County

Windham County Cottages information

Number of reviews
10
Accommodation
92 Cottages
Lowest Price
10.804.611 ₫
Highest Price
10.804.611 ₫