What are the top rated Cottage Rentals in Windham?

There are a lot of options in Windham. If you plan on staying in the Windham 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: <a href="/property/dancing-horse-farm-in-windham-spectacular-9-bedroom-home-30-acres-ski-lodge/HA-121207951" class="class="static-page-link"">Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge</a> <a href="/property/charming-mountain-retreat-lg-mod-kit-on-stream-fire-pit-hot-tub/HA-3211199316" class="class="static-page-link"">Charming Mountain Retreat Lg Mod/Kit on Stream/Fire-pit/Hot Tub</a> <a href="/property/private-pickleball-ct-indoor-hot-tub-spa-room-lift-tkts/HA-121172309" class="class="static-page-link"">Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts</a> <a href="/property/cozy-caboose-in-the-city/HA-3211850836" class="class="static-page-link"">Cozy Caboose in the city</a> <a href="/property/windham-log-cabin-on-35-acres-family-friendly/HA-321870658" class="class="static-page-link"">Windham Log Cabin on 35 Acres. Family friendly.</a> <a href="/property/walk-to-slopes-at-windham-great-ski-home-for-families-golf-bike-hike-too/HA-1213966641" class="class="static-page-link"">Walk to slopes at Windham! Great ski home for families. Golf, bike, &amp; hike too.</a> <a href="/property/cutest-cabin-in-windham-close-to-ski-slope-and-ski-town/HA-1213477551" class="class="static-page-link"">Cutest Cabin in Windham close to ski slope and ski town</a> <a href="/property/timber-frame-home-only-5-minutes-from-windham-mountain-perfect-for-2-families/HA-1217897809" class="class="static-page-link"">Timber frame home only 5 minutes from Windham Mountain - perfect for 2 families!</a> <a href="/property/gut-reno-4-season-nirvana-hot-tub-wifi-fire-pit-fireplace-windhm-mtn-view-2bbqs/HA-321488597" class="class="static-page-link"">*GUT RENO 4 Season Nirvana*Hot Tub*WiFi*Fire Pit*Fireplace*Windhm Mtn View*2BBQs</a> <a href="/property/windham-family-getaway/HA-3211835606" class="class="static-page-link"">Windham Family Getaway</a>

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

The average cost for a cottage rental in Windham is $286 per night. Execstays has a wide list of great cottages near Windham that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Windham that allow pets?

Yes, here are the top cottage rentals in Windham that allow you to bring your pet: Tiny House on Walnut Grove Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge Fantastic 2 family vacation home with EV charger Antique Rose Inn Windham TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores <a href="/all/usa/new-york/windham" class="class="static-page-link"">See all pet-friendly vacation rentals in Windham on Execstays</a>

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

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

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

As of 2026, the data from Execstays shows that there are Over 1 private swimming pools or cottages with indoor pools in the Windham area along with other great amenities.