Vacation rentals in Windham County

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Popular amenities for Windham County vacation rentals

Other great vacation rentals in Windham County

Guest favorite
A clear white sign with bold black lettering reading 'ENTRANCE' is displayed, hanging from a decorative metal bracket. Lush greenery from surrounding trees is visible in the background, adding to the inviting natural setting.
Guest suite in Dover
4.88 out of 5 average rating, 17 reviews

The Eagles Nest - Private Apartment

AlisonRating, 5 stars2 months ago
This is a lovely place, very close from mountain snow. We went skiing and the location is perfect. So clean and very easy to find and get in. They let us use the laundry and it’s so cozy ❤️
Guest favorite
The cottage exterior features a wooden facade with a green metal roof, framed by vibrant trees. A covered porch with potted flowers welcomes visitors, while large windows allow natural light to fill the space. The peaceful setting highlights the connection to nature.
Cabin in Guilford
4.96 out of 5 average rating, 69 reviews

Guilford Grove Cottage

BobRating, 5 stars1 week ago
Joel's place is exactly as described in the listing. The cabin more than met our needs. It was very clean, the bed was so comfortable, the shower had good pressure and enough hot water for the two of us, and the location is peaceful and quiet. We hope to return in the future.
Guest favorite
A wooden deck features a fire circle and two comfortable chairs, positioned amidst nature. The cozy cabin, with a brown exterior and large windows, is surrounded by greenery and sunflowers, providing a serene outdoor space for relaxation.
Tiny home in Jamaica
5 out of 5 average rating, 6 reviews

Chapel of Love - Tiny House Life

SuleidyRating, 5 stars1 month ago
Great place to stay. The place is quiet, peaceful, private and comfortable. I loved staying here.
Guest favorite
A fire pit is surrounded by stones, with flames flickering in front of a rustic cabin nestled among trees. A car is parked nearby, and a picnic table is positioned in the yard, creating a cozy outdoor gathering space.
Cabin in Jamaica
4.9 out of 5 average rating, 392 reviews

Cabin 7min to Ski Stratton-Wood Stove,Views,DogsOK

BenRating, 5 stars2 weeks ago
The place was nice, very well depicted from Airbnb. Jason is very responsive and a good host!
Guest favorite
A warm wood-paneled interior features a cozy seating area with a bench and a rocking chair. Large windows provide views of the surrounding forest, while a patterned area rug and a vintage lamp add to the rustic charm.
Cabin in Brookline
4.94 out of 5 average rating, 16 reviews

Off-the-Grid Cabin in the Forest

TomRating, 5 stars8 months ago
We absolutely love this cabin. It's perfect!!!
Top guest favorite
The entrance of the building is illuminated by two wall-mounted lanterns, casting a soft glow. The large double doors are a dark shade, while colorful stained glass can be seen through the arched windows on either side, highlighting the architectural details.
Guest suite in Brattleboro
4.94 out of 5 average rating, 583 reviews

Charming studio in renovated 19th century church.

TusharRating, 5 stars1 week ago
Liza and Rick have an incredible place - beautiful, spotless, delightfully charming. They were wonderful hosts - thoughtful and caring, and incredibly easy to communicate with. Highly recommend!
Top guest favorite
Guesthouse in Dummerston
5 out of 5 average rating, 15 reviews

Cottage amongst the trees

MattRating, 5 stars4 days ago
John& Aisha’s cottage was the perfect place for our weekend getaway. Conveniently located between Putney and Brattleboro made it easy to get around. The cottage was very clean and well stocked. John and Aisha were super hosts and went above and beyond with local recommendations to activities we could do. Would highly recommend to anyone traveling through VT.
Guest favorite
A grassy area features two wooden chairs and a loveseat positioned around a stone firepit. The rustic cabin structure stands nearby, showcasing multiple windows and a wooden exterior. Surrounding trees create a natural setting, enhancing the sense of privacy.
Tiny home in Townshend
4.98 out of 5 average rating, 63 reviews

Cheerful cabin retreat in the woods and mountains

CarinaRating, 5 stars2 months ago
My pup and I had a great escape from Boston, and this cabin was the perfect place to land and take in the beautiful scenery outside every window. The screened-in porch and lofted bed are adorable, and my pup and I loved the wood stove. The cabin is equipped with everything, there is a store nearby, and it had a lot of convenient dog items as well. I was glad that I had my Subrau on the mountain roads since it was a rainy weekend. Thanks so much!

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