What are the top rated Cottage Rentals in Windham County?

There are a lot of options in Windham County. If you plan on staying in the Windham County area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Windham County: <a href="/property/pristine-west-dover-home-w-deck-mountain-views/EP-94470784" class="class="static-page-link"">Pristine West Dover Home w/Deck &amp; Mountain Views!</a> <a href="/property/jamaica-vacation-home-w-deck-8-mi-to-skiing/EP-98549051" class="class="static-page-link"">Jamaica Vacation Home w/Deck: 8 Mi to Skiing!</a> <a href="/property/8-mi-to-mount-snow-rustic-marlboro-cottage/BC-12129614" class="class="static-page-link"">8 Mi to Mount Snow Rustic Marlboro Cottage</a> <a href="/property/vermont-sugar-house-guesthouse-for-glamping/HA-3213146100" class="class="static-page-link"">Vermont Sugar House Guesthouse for Glamping</a>

How much does it cost to rent a cottage in Windham County?

The average cost for a cottage rental in Windham County is $408 per night. Villa Bay has a wide list of great cottages near Windham County that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Windham County that allow pets?

Yes, here are the top cottage rentals in Windham County that allow you to bring your pet: The Cairn, 1840s Cozy Stone Cottage, Pet Friendly Magical Retreat Cottage, 15 min from Mt Snow skiing Wilmington Retreat Near Trails, Skiing & Festivals Rare new Home on Lake Whitingham. Semi-priv beach <a href="/all/usa/vermont/windham-county" class="class="static-page-link"">See all pet-friendly vacation rentals in Windham County on Villa Bay</a>

Do you have any rental cottages in Windham County that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Windham County to find one that works for you.

Are there quality cottages in Windham County that have indoor swimming pools?

As of 2026, the data from Villa Bay shows that there are Over 28 private swimming pools or cottages with indoor pools in the Windham County area along with other great amenities.

Windham County Cottage Rentals By Owner

The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

From US $236

10.0 (18 Reviews)

Cottage

The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

Air Conditioner
Parking
Pet Friendly

Windham County Cottage Rentals & Holiday Homes

Find the best cottages in Windham County - We found 28 exact matches

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