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Popular penthouses
Southern Vermont Retreat and Set for multiple purposes
4.5 miles from Windham, VT25 guests
Weekend or Whole Week events for intimate groups Inn and Lodge.
The lodge has 8 well appointed rooms king, queen and twin bed options. 4 are suites with an extra room.
The communal kitchen and large parlor room in separate location
...
From
$150
/hr
12 hr min
Mid-Century Modern A-frame
5.3 miles from Windham, VT50 guests
This is a 1970's A Frame that is newly renovated with mid century modern touches. The original barn wood paneling brings a cozy and unique environment to capture any moment. The home is nestled amongst trees and overlooks a large pond. The entire home
...
From
$140
/hr
4 hr min
Magical Mountain House
Serving the Windham, VT area25 guests
The 7 bedroom, 3 bathroom two family house is on an unpaved road on the middle of the woods and is surrounded by 10 acres of land. There are three more houses down the road, until it turns into a trail. Many who visit
...
From
$500
/hr
4 hr min
Valley View Villa – Rustic VT Luxury w/ Pond
Serving the Windham, VT area50 guests
Large, cozy modern farmhouse on 5+ sprawling acres of property featuring a pond stocked with fish, private hiking trails in the woods, a large grassy yard, and amazing views of the nearby hills and mountains. The villa boasts modern amenities while maintaining its cozy, rustic
...
From
$143
/hr
4 hr min
Mixture of classic New England with Mid Century and Scandinavian modern
Serving the Windham, VT area25 guests
The house is 5 bedroom, 3.5 bathroom with a large rear deck and a hottub. It's situated on 35 private acres with 2 ponds, a stone patio/beach and a stone firepit pondside. There are also hiking trails throughout the property.
Please inquire via Peerspace messaging
...
From
$250
/hr
4 hr min
Similar searches in Windham, VT
Updated June 4, 2026Our data is refreshed in real time using booking trends, verified guest reviews, and direct partner updates — with additional quality checks from our team.