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Vacation rentals in Windham

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Top-rated vacation rentals in Windham

Guests agree: these stays are highly rated for location, cleanliness, and more.

Barn in Chester
Inviting studio apartment above barn in Vermont
This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. We are as close or as far away as you would like us to be with our house right next door.
$79 per night
Home in Townshend
Lawrence Cottage
Deep in the West River Valley region of Windham County, Lawrence Cottage has a gorgeous setting upon Windham Hill. If you long for serenity and beauty, we have the perfect escape for you. We are convenient to all local amenities and activities and an easy drive from Boston or New York. We are near Townshend, Jamaica and Lowell Lake State Parks, Magic Mountain, Mount Snow and Stratton Mountain Resorts. This is Vermont--of course we welcome people of all backgrounds.
$109 per night
Apartment in Townshend
Private Apt. on Farm, great views and Hot tub,
Self-contained apt with fantastic views, outside deck & private entrance with keypad lock. Two queen bedrooms and queen sleeping loft, kitchen and open plan living room. Located on a historic 38-acre working farm. If you need more space we have an adjoining apartment that sleeps 5. Apartment is above garage and attached to the main farmhouse. Pls note pricing is based on up to four guests; add'l $25/person/night up to max 6 guests added automatically.
$145 per night

Stay near Windham's top sights

Magic Mountain Ski Area136 locals recommend
Hamilton Falls27 locals recommend
The Upper Pass Lodge3 locals recommend
The Red Slate Restaurant4 locals recommend
West River Dam3 locals recommend
Tater Hill Golf Course8 locals recommend

Other great vacation rentals in Windham

Apartment in Londonderry
Vermont Getaway Apartment-See Fall Special!
$108 per night
Tiny home in Chester
Sage House and Camp Wildwood Vermont - w/ sauna!
$144 per night
Tiny home in Athens
Luxury “Tiny” House, Immersed In Nature (Timbery)
$260 per night
Home in Weston
Reillys Rest -GreenMtns! Secluded-Pet-Kid friendly
$140 per night
Guesthouse in Putney
Cozy cottage loft and retreat
$100 per night
Tiny home in Jamaica
Apple Blossom Cottage: A Tiny House
$98 per night
Apartment in Jamaica
The Getaway
$136 per night
Cabin in Stratton
Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi
$198 per night
Apartment in Andover
Private Hilltop farm apartment
$98 per night
Home in Windham
Artistic Southern Vt Countryside Home at Windham
$199 per night
Apartment in Londonderry
Dog-friendly, 1-bedroom apartment w/ fireplace (A)
$199 per night
Condo in Londonderry
Magical Ski-In/Ski-Out Condo at Magic w/ game room
$93 per night

Quick stats about vacation rentals in Windham

Total rentals

50 properties

Rentals with dedicated workspaces

30 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

40 properties are a good fit for families

Total number of reviews

1.5K reviews

Nightly prices starting at

$90 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Windham County
  5. Windham