Cottages in Windham County
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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

A snow-covered road winding through a forested area with buildings and mountains in the background.

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Our top choices for Windham County cottages

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

A two-story house with a covered porch and a small deck, surrounded by a grassy yard and tall trees.

A cabin with a deck overlooking a forested area.

A spacious dining area with a large table and chairs, a fireplace, and a view of the outdoors.

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)

10/10

Exceptional

(1 review)

"Beautiful home, spacious, huge back yard. Close to everything you need. Hoping to return soon!!"

Jacqueline

West Dover Home - 3 Miles to Mount Snow Resort!

A covered porch with white railings and two rocking chairs.

A spacious living room with wooden floors, a sofa set, a rocking chair, and a fireplace.

A cozy living room with wooden furniture, a sofa, a coffee table, and a bookshelf.

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 stone fireplace with a flat-screen TV above it, a wooden floor, a bed with white bedding, and a view of the outdoors through a window.

A living room with a stone fireplace, wooden flooring, a television on the mantel, and leather furniture.

A kitchen with a white refrigerator, wooden cabinets, a coffee maker, and a toaster.

3. '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)

10/10

Exceptional

(1 review)

"Amazing place! Super clean and cozy, and host was extremely nice and communicative. Highly recommend."

Alexander

'mount Pine' Winter Escape Near the Green Mtns!

A two-story house with a covered patio, a separate garage, and a well-maintained lawn.

A spacious kitchen with a large wooden dining table, modern appliances, and a cozy living area with a sofa and windows.

A living room with a fireplace, a television mounted above it, and a sofa.

A spacious kitchen with a large island, wooden bar stools, and pendant lighting.

4. 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)

10/10

Exceptional

(2 reviews)

"This place was absolutely perfect, very clean and very well taken care of."

Charles

Spacious Home,ppong,darts,pick Ball Net, 6mi mt sn

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

5. 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

A wooden deck with a table and chairs, surrounded by trees with autumn foliage.

A restaurant with wooden beams, high ceilings, and a long counter with bar stools.

An indoor swimming pool with wooden beams, a green slide, and lounge chairs.

A room with a wooden bench, a green wall, and a clock. There are chairs outside the door and a sign on the wall.

6. 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 wooden cabin with a balcony, surrounded by trees and a grassy hill.

A wooden deck with a picnic table and a railing.

A wooden dining table with chairs, a window with blinds, and a view of trees outside.

A spacious living area with a large sectional sofa, a wooden staircase, and a kitchen in the background.

7. 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

A wooden cabin with a metal roof, a hot tub, and a bench in a forested area.

A cozy living room with a stone fireplace, a blue sofa, and a large window with curtains.

A rustic kitchen with wooden cabinets, a stone wall, and a refrigerator with a ski-themed magnet.

A rustic wooden cabin with a hot tub, a wooden deck, and a fenced area.

8. 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

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

A kitchen with wooden beams, a large island, and a dining area with blue upholstered chairs.

A cozy cabin interior with a wooden ceiling, a television on a cabinet, a sofa with cushions, and a door leading outside.

A wooden cabin interior with a dining area, large windows, and potted plants.

9. 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)

10/10

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 ❤️"

sarah

Hiking Trails On-site: Cozy Falls Brook Cabin

A red building with a green roof, white porch, and a sign that reads "Studio."

A kitchen with a white stove, wooden cabinets, and a large window.

A spacious living room with a high ceiling, a kitchen area, and a dining area with red and white Adirondack chairs.

A cozy interior with a kitchen area, a dining table, and a bookshelf.

10. 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)

10/10

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."

gloria

Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!

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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Hotels with indoor pool in Bennington
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Bennington Hotels
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Brattleboro Hotels
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Castleton Hotels
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Chester Hotels
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Dorset Hotels
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Fair Haven Hotels
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Grafton Hotels
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Hotels near Green Mountain National Forest
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Hotels near Green Mountain Rock Climbing Center
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Hotels near Green Mountain Rock Climbing Center
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Ludlow Hotels
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Marlboro Hotels
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Resorts in Marlboro
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Apartments in North Bennington
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Norwich Hotels
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Peru Hotels
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Plymouth Hotels
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Hotels with Gyms in Rutland
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Hotels with Spa in Rutland
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Sharon Hotels
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Resorts in Sharon
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Springfield Hotels
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Hotels near The Ice House Ice Skating
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Wallingford Hotels
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Wardsboro Hotels
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Wells Hotels
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West Townshend Hotels
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White River Junction Hotels
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Wilmington Hotels
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Windham Hotels
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Woodstock Hotels
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Flights to Central Vermont
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Flights to Grafton
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Flights to Putney
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Flights to Shrewsbury
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Flights to Southern Vermont
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Flights from West Dover
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Flights from Peru
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Flights from Jamaica
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Flights from Gaysville
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Flights from Glastenbury
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Flights from East Dover
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Flights from Hartford (BDL) to Rutland (RUT)
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Flights from Burlington (BTV) to Rutland (RUT)
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Flights from Chicago (DPA) to Springfield (VSF)
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Flights from Enschede (ENS) to Rutland (RUT)
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Flights from Khajuraho (HJR) to Rutland (RUT)
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Flights from Ibiza (IBZ) to Rutland (RUT)
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Flights from Columbus (LCK) to Springfield (VSF)
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Flights from Milwaukee (MKE) to Rutland (RUT)
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Flights from Modesto (MOD) to Rutland (RUT)
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Flights from Manston (MSE) to Rutland (RUT)
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Flights from Misawa (MSJ) to Rutland (RUT)
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Flights from Coca (OCC) to Rutland (RUT)
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Flights from Santa Maria (RIA) to Rutland (RUT)
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Flights from St. George (SGU) to Rutland (RUT)
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Flights from Saranac Lake (SLK) to Springfield (VSF)
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Flights from Traverse City (TVC) to Rutland (RUT)
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Ball Mountain State Park
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Buzzy Park
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Diamond Run Mall
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Visit East Dover
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Fire Tower
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Gifford Woods State Park
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Green Mountain National Golf Course
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Hooker-Dunham Theater & Gallery
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Jamaica Holidays
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Killington Golf Course
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Killington Peak
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Killington Holidays
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Visit Killington
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Lowell Lake State Park
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Main Street Museum
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Visit Marlboro
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Mclaughlin Falls
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Pico Mountain at Killington Ski Resort
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Visit Proctor
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Quechee Holidays
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Visit Quechee
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Skye Peak Express Quad Ski Lift
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Snow Lake
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Snow Stars Carpet
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Stratton Mountain Resort
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Sunrise Village Triple Ski Lift
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Vermont Country Store
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White River Junction Holidays
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Yellow Barn
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Car hire Athens
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Things to do in Bennington
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Cottages in Windham County

Change your mind

Treat yourself

Be picky

Top cities in Windham County

West Dover

Find holiday rentals that suit your style

Check prices for these dates

Our top choices for Windham County cottages

1. West Dover Home - 3 Miles to Mount Snow Resort!

2. 4 Mi to Lake Raponda! Secluded Family Cottage

3. 'mount Pine' Winter Escape Near the Green Mtns!

4. Spacious Home,ppong,darts,pick Ball Net, 6mi mt sn

5. Spacious Vermont Farmhouse 3 Mi to Mount Snow

6. Wilmington Vacation Rental Near Hiking and Skiing!

7. Cozy Mountain Retreat w/ Deck ~ 3 Mi to Mount Snow

8. 4 Mi to Stratton Mountain Resort! Cabin w/ Hot Tub

9. Hiking Trails On-site: Cozy Falls Brook Cabin

10. Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!

Explore a world of travel with Expedia