
Holiday houses in Windham County
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Top-rated holiday rentals in Windham County
Guests agree: these stays are highly rated for location, cleanliness and more.
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Top Guest favourite

Guest suite in Wilmington
4.92 out of 5 average rating, 774 reviewsArchitectural GuestSuite
GregRating, 5 stars2 weeks ago
What a lovey place to stay! You can’t beat the location and the hosts went above and beyond making such a creative space. Make sure you read the description. There isn’t a tv and the windows make it bright in the morning but we loved it all the more for it. I wish we could have stayed longer and if we are coming back through we will definitely stay again! Host was great and super helpful. We walked down to Dots for breakfast in the morning and truly enjoyed our time in Wilmington.
Guest favourite

Cabin in Guilford
4.96 out of 5 average rating, 73 reviewsGuilford Grove Cottage
JulieRating, 5 stars4 days 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

Tiny home in Athens
4.9 out of 5 average rating, 120 reviewsLUXE Forest Retreat
AaronRating, 5 stars1 month ago
Great experience. The house is perfect for a relaxing stay and has everything necessary for cooking, making a campfire, or enjoying a movie inside. Would definitely recommend!
Guest favourite

Condo in Dover
4.95 out of 5 average rating, 61 reviewsCondo w/ great amenities 4-seasons! Ski in Ski out
BrianRating, 5 stars2 days ago
Christine was a great host. The condo was as described. The place was clean and well organized, very cute and cozy. Christine was very responsive and helpful. I will definitely stay here again.
Top Guest favourite

Home in East Dover
5 out of 5 average rating, 50 reviewsMagical Retreat Cottage - Waterfalls Everywhere
DavidRating, 5 stars3 days 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.
Guest favourite

Guest suite in Putney
4.96 out of 5 average rating, 69 reviewsPeaceful Country Retreat on 15 Secluded Acres
MelanieRating, 5 stars2 days ago
We loved our stay ! It was located in a semi secluded location that is surrounded by woods . So waking up to the sound of rain or just nature is what you are going to get . 10 minutes from Putney Downtown area and about 20 minutes from Brattleboro . If you want peaceful sleep and even if you just want to get away to a serene spot . This is great !
Destinations to explore
- Rentals with a kayak Windham County
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- Rentals with a fireplace Windham County
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- Ski-in/ski-out rentals Windham County
- Rentals with lake access Windham County
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- Rentals with an accessible height toilet Windham County
- Rentals with a fire pit Windham County
- Family-friendly rentals Windham County
- Rentals with a sauna Windham County
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- Farmstay rentals 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