Search Windham County Cottages

Compare and save

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jan 30 - Feb 1
In two months
Mar 13 - Mar 15
In three months
Apr 10 - Apr 12
In four months
May 8 - May 10

Top Cities in Windham County

We were pretty impressed with this. Never seen a frozen body of water strong enough for all of this activity!
CottagesCottages

Brattleboro

Brattleboro

Our top choices for Windham County cottages

Exterior

Cottage in Wilmington

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
8.6 out of 10, Excellent, (64 reviews)
"Can recommend"
United States
Niklas H.
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Exterior

Cottage in Chester

The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
10.0 out of 10, Exceptional, (19 reviews)
"The house is absolutely beautiful - Check in super easy"
United States
Dawn J.
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
Exterior

Cottage in Londonderry

Vermont Country Cottage (Near Village)
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

Cottage in Wilmington

Rare new Home on Lake Whitingham. Semi-priv beach
10.0 out of 10, Exceptional, (6 reviews)
"Very nice place."
United States
michael r.
Rare new Home on Lake Whitingham. Semi-priv beach
House (3 Bedrooms) | Interior

Cottage in Wilmington

Near Hiking & Skiing: Home in Wilmington!
3.0 star property
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 (4 Bedrooms) | Interior

Cottage in West Wardsboro

Near Skiing & Hiking: Quiet Home in West Wardsboro
3.0 star property
Near Skiing & Hiking: Quiet Home in West Wardsboro
House (2 Bedrooms) | Interior

Cottage in Brattleboro

Hiking Trails On-site: Cozy Falls Brook Cabin
3.0 star property
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 (3 Bedrooms) | Interior

Cottage in Wilmington

Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
3.0 star property
10.0 out of 10, Exceptional, (1 review)
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
House (3 Bedrooms) | Interior

Cottage in Wardsboro

'mount Pine' Winter Retreat Near the Green Mtns!
3.0 star property
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 (5 Bedrooms) | Interior

Cottage in Whitingham

Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
3.0 star property
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
House (3 Bedrooms) | Interior

Cottage in Wilmington

Wilmington Retreat Near Trails, Skiing & Festivals
3.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"Great location and awesome house. Owners were easy to communicate with. "
United States
Anonymous traveler
Wilmington Retreat Near Trails, Skiing & Festivals
House (5 Bedrooms) | Interior

Cottage in Jacksonville

'john's Farmhouse in Mount Snow' on 120 Acres!
3.0 star property
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 (1 Bedroom) | Front of property

Cottage in Vernon

Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
3.0 star property
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 (4 Bedrooms) | Interior

Cottage in Putney

Charming Putney Home: Porch, Grill & Hiking Trails
3.0 star property
Charming Putney Home: Porch, Grill & Hiking Trails
Interior

Cottage in Wilmington

2 Mi to Golfing & Hiking: Spacious Wilmington Home
3.0 star property
10.0 out of 10, Exceptional, (1 review)
"This place was absolutely perfect, very clean and very well taken care of."
United States
Charles
2 Mi to Golfing & Hiking: Spacious Wilmington Home
Exterior

Cottage in Newfane

Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow
9.6 out of 10, Exceptional, (68 reviews)
"I was a solo traveler because my companion had to change plans, so I had the benefit of complete piece of mind at this place, and more room than I needed. It really is a beautiful place with a nice view. Very quiet and peaceful, it was a nice location to get away from the city. Only 4 minutes from Rock River, so that was a nice bonus. I'm looking forward to returning here in the future for sure "
United States
John W.
Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow
House (4 Bedrooms) | Interior

Cottage in Wilmington

Wilmington Vacation Rental Near Hiking and Skiing!
3.0 star property
Wilmington Vacation Rental Near Hiking and Skiing!
House (4 Bedrooms) | Front of property

Cottage in West Dover

West Dover Vacation Rental w/ Hot Tub Near Mt Snow
3.0 star property
West Dover Vacation Rental w/ Hot Tub Near Mt Snow
House (3 Bedrooms) | Interior

Cottage in Wilmington

Hike, Ski & Relax: Renovated Retreat in Wilmington
3.0 star property
Hike, Ski & Relax: Renovated Retreat in Wilmington
House (3 Bedrooms) | Interior

Cottage in Londonderry

Londonderry Chalet w/ Deck, Fire Pit & Views!
3.0 star property
Londonderry Chalet w/ Deck, Fire Pit & 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windham County Hotel Reviews

Inn At Mount Snow

Inn At Mount Snow

10/10 Excellent
"Staff is so friendly and helpful. Very cool lodge."
Jeffrey 1-night trip
Posted 4 days ago
Inn At Mount Snow

Find out more about Windham County

Windham County Cottages information

Number of reviews
142
Accommodation
97 Cottages
Lowest Price
Highest Price

Explore a world of travel with Expedia