
Holiday rentals in Windham County
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Top-rated holiday rentals in Windham County
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Popular amenities for Windham County holiday rentals
Other great holiday rentals in Windham County
Top guest favourite

Guest house in Marlboro Township
4.97 out of 5 average rating, 162 reviewsRefined, serene and like no other, Marlboro, VT.
Top guest favourite

Home in East Dover
5 out of 5 average rating, 53 reviewsMagical Retreat Cottage - Waterfalls everywhere
Top guest favourite

Cottage in Dover
4.96 out of 5 average rating, 242 reviewsCozy private cottage in the woods of Vermont
Top guest favourite

Guest house in Dummerston
5 out of 5 average rating, 16 reviewsCottage amongst the trees
Top guest favourite

Chalet in Wardsboro
5 out of 5 average rating, 15 reviewsModern Lux Cabin w/ Mtn Views | Fire Pit
Guest favourite

Cabin in Jamaica
4.94 out of 5 average rating, 65 reviewsThe Woodland A-Frame
Guest favourite

Tiny home in Townshend
4.98 out of 5 average rating, 66 reviewsCheerful cabin retreat in the woods and mountains
Guest favourite

Tiny home in Chester
5 out of 5 average rating, 30 reviewsTiny A-Frame Rest House in Woods
Destinations to explore
- Rentals with pools Windham County
- Family-friendly rentals Windham County
- Townhouse rentals Windham County
- Beachfront rentals Windham County
- Rentals with beach access Windham County
- House rentals Windham County
- Chalet rentals Windham County
- Rentals with breakfast Windham County
- Pet-friendly rentals Windham County
- Rentals with a washing machine and dryer Windham County
- Rentals with an accessible-height toilet Windham County
- Farm stay rentals Windham County
- Rentals with lake access Windham County
- Rentals with a kayak Windham County
- Ski-in/ski-out rentals Windham County
- Rentals with a hot tub Windham County
- Rentals with a fireplace Windham County
- Apartment rentals Windham County
- Rentals with a firepit Windham County
- Private suite rentals Windham County
- Fitness-friendly rentals Windham County
- Rentals with outdoor seating Windham County
- Rentals with a patio Windham County
- Flat rentals Windham County
- Rentals with an EV charger Windham County
- Family-friendly rentals Windham County
- Waterfront rentals Windham County
- Tiny house rentals Windham County
- Cabin rentals Windham County
- Rentals with a sauna Windham County
- Bed and breakfasts Windham County
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- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Monadnock State Park
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Pico Mountain Ski Resort
- The Shattuck Golf Club
- Magic Mountain Ski Resort
- Dorset Field Club
- Stratton Mountain Resort
- Mount Sugarloaf State Reservation
- Bousquet Mountain Ski Area
- Hildene, The Lincoln Family Home
- Bretwood Golf Course
- Bromley Mountain Ski Resort
- Hancock Shaker Village
- Northern Cross Vineyard
- Pineridge Cross Country Ski Area
- Clarksburg State Park
- Baker Hill Golf Club
- Fox Run Golf Club