
Holiday houses in Windham County
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Top-rated holiday rentals in Windham County
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Other great holiday rentals in Windham County
Guest favourite

Cabin in Guilford
4.96 out of 5 average rating, 73 reviewsGuilford Grove Cottage
JulieRating, 5 stars1 week ago
Joel's place was impeccably clean and free of clutter. The shower pressure was excellent. The kitchen had everything you need ro cook, and it was a treat to have milk, eggs, english muffins and coffee available for breakfast as well as tea which you can enjoy sitting out on the porch. It is a short drive to Brattleboro and the surrounding area is exquisitely beautiful.
Guest favourite

Guest suite in Dover
4.91 out of 5 average rating, 22 reviewsThe Eagles Nest - Private Apartment
ValerieRating, 5 stars5 days ago
Wonderful spot to stay, my daughter was thrilled to meet the little eagle stuffy and we really enjoyed the space. Wish we could have stayed longer!!
Top Guest favourite

Guest suite in Guilford
4.97 out of 5 average rating, 152 reviewsPrivate, Quiet Vermont Studio With Mountain Views
KatherineRating, 5 stars1 week ago
We had such a fantastic evening staying here! We were on a road trip and this was one of our spots. Although it is far from anything, the scenery is absolutely stunning! I recommend to anyone trying to get the peacefulness of vermont on their trip!
Guest favourite

Chalet in Dover
4.97 out of 5 average rating, 118 reviewsMountain Chalet: Private Brook - Hot Tub - Firepit
LuisRating, 5 stars2 weeks ago
Danielle and Ben were excellent hosts and their guide was really helpful and informative for us who had never been to Vermont or the area! We really enjoyed spending time in the location and it was only made better by returning to their beautiful and peaceful home. The place is even better than the pictures, everything was exactly as described, and we had plenty of spaces to choose from for alone time and gathering time with our group. Danielle and Ben remained communicative throughout and proactive with info we needed for check-in. We will certainly be back to Vermont and we know exactly the place to go for the most elevated and serene experience possible. Thank you!!
Top Guest favourite

Home in East Dover
5 out of 5 average rating, 50 reviewsMagical Retreat Cottage - Waterfalls Everywhere
DavidRating, 5 stars1 week ago
Gene’s house is a place of peaceful quiet and beauty. It’s well appointed and comfortable, with wireless and all the various conveniences, but it’s far more than that. The separation between the interior and the beautiful meadow and forest outside dissolves through Gene’s use of windows and glass doors, and the calming sound of falling water can be heard in every room. His use of color and symmetry create an environment that allows you to decompress, and as a result, you can’t help but to connect with the beauty of the forest. The waterfalls are wonderful to sit by; it was too early in the season for a swim in a cold mountain stream, but that’s just me. The design and setting of the home is a reflection of Gene. If you visit, I recommend that you get to know him a bit. His kind attentiveness makes him a first-rate host, but it’s part and parcel of his uncommon connection to the world around him. Gene was more than a host to us- he became a true friend. We will be back.
Guest favourite

Cabin in Brookline
4.94 out of 5 average rating, 17 reviewsOff-the-Grid Cabin in the Forest
AndrewRating, 5 stars3 weeks ago
Ideal cabin in the woods for a secluded forest getaway - well stocked kitchen, and the outhouse is 10/10. Very responsive and helpful!
Top Guest favourite

Guesthouse in Dummerston
5 out of 5 average rating, 16 reviewsCottage amongst the trees
MattRating, 5 stars2 weeks 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.
Top Guest favourite

Yurt in Dover
5 out of 5 average rating, 35 reviewsMount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger
MaxineRating, 5 stars6 days ago
Beautiful home Amazing views Enjoyed our stay Bummer that sauna was under repair Was looking forward to the sauna Enjoyed hot tub
Destinations to explore
- Rentals with beach access Windham County
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- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- The Shattuck Golf Club
- Dorset Field Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Baker Hill Golf Club
- Bousquet Mountain Ski Area
- National Museum of Racing and Hall of Fame
- Pineridge Cross Country Ski Area
- Clarksburg State Park
- Ekwanok Country Club
- Bretwood Golf Course