Cottages in Windham County

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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for Windham County cottages

House (5 Bedrooms) | Interior

Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!

Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
3.0 star property
Whitingham
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
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 (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)
"Great winter gateaway at the mountains, close to mount snow, closed garage, lots of space and an authentic Vermont house. Indoor garage."
United States
sahin
10 Mi to Mt Snow! Grand Estate Built to Entertain
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 (4 Bedrooms) | Interior

3 Mi to Mount Snow: Spacious West Dover Home

3 Mi to Mount Snow: Spacious West Dover Home
3.0 star property
West Dover
3 Mi to Mount Snow: Spacious West Dover Home
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
Hiking Trails On-site: Cozy Falls Brook Cabin
House (4 Bedrooms) | Interior

Ski, Golf & Hike: Spacious Dover Retreat!

Ski, Golf & Hike: Spacious Dover Retreat!
3.0 star property
West Dover
Ski, Golf & Hike: Spacious Dover Retreat!
House (3 Bedrooms) | Interior

2 Mi to Mt Snow: Warm & Cozy Family Winter Retreat

2 Mi to Mt Snow: Warm & Cozy Family Winter Retreat
3.0 star property
West Wardsboro
2 Mi to Mt Snow: Warm & Cozy Family Winter Retreat
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

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

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) | Interior

Cozy Log Cabin Near Mt Snow: Views, Modern Comfort

Cozy Log Cabin Near Mt Snow: Views, Modern Comfort
3.0 star property
Wilmington
Cozy Log Cabin Near Mt Snow: Views, Modern Comfort
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!
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 (2 Bedrooms) | Interior

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
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 (4 Bedrooms) | Interior

Near Skiing & Hiking: Quiet Home in West Wardsboro

Near Skiing & Hiking: Quiet Home in West Wardsboro
3.0 star property
West Wardsboro
Near Skiing & Hiking: Quiet Home in West Wardsboro
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) | 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
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

The Putney Inn

The Putney Inn

10/10 Excellent
"Parking was available and easy, and it felt safe. Breakfast was slightly limited (boiled eggs, for example, would be a welcome breakfast item to enjoy with toast and the good coffee), but the fresh waffle was delicious, as well as the fruit and yogurt. The room was spotless, and the manager and his personnel excellent. "
Daniela 2-night trip
Posted 15 hours ago
The Putney Inn

Find out more about Windham County

Windham County Cottages information

Number of reviews
10
Accommodation
87 Cottages
Lowest Price
Highest Price