Windham Vacation Rentals

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Vacation Rentals in Windham

Brand New 2 Bdr. Townhome Minutes from Windham Mtn

Hensonville NY

$339 nightly

$366 total

Jun 10 - Jun 11

Total with taxes and fees

With a stay at this vacation home in Hensonville, you'll be in the mountains, within a 15-minute drive of Hunter Mountain and Windham Country Club.

Kitchen

Washer

Sauna, Hot-tub, fire-pit, pet friendly. Private Pool. Mountain views!

LANESVILLE NY

When you stay at this vacation home in Lanesville, you'll be in the mountains, within a 15-minute drive of Catskill Mountains and Hunter Mountain.

Pool

Hot Tub

Cozy cabin with great views and fire place!

Fleischmanns NY

With a stay at this vacation home in Fleischmanns, you'll be within a 10-minute drive of East Branch Delaware River and Pakatakan Farmers' Market.

Parking available

Barbecue grill

Windham Mountain Chalet with Treehouse sleeps 15, Game Room & fireplace

Windham NY

With a stay at this vacation home in Windham, you'll be in the mountains, within a 10-minute drive of Windham Mountain Resort and Catskill State Park.

Kitchen

Washer

Free 50 Amp EV Charger Modern New, HotTub, A/C, Webber Grill, 2 Decks, FirePit

Fleischmanns NY

With a stay at this vacation home in Fleischmanns, you'll be within a 15-minute drive of Catskill Mountains and Catskill State Park.

Hot Tub

Kitchen

Private Getaway 10 Mins From Hunter & Windham Mountain

Jewett NY

With a stay at this vacation home in Hunter, you'll be within a 15-minute drive of Hunter Mountain and Windham Mountain Resort.

Hot Tub

Kitchen

The Moon House Dome: 10 min away from skiing and golfing. Waterfront. Fishing.

Acra NY

Located in Acra, this vacation home is within a 10-minute drive of Cairo Town Hall and Angelo Canna Town Park.

Hot Tub

Kitchen

A world where time stands still, close to Belleayre Ski & Wedding venues.

City Roxbury NY

$409 nightly

$449 total

Jun 11 - Jun 12

Total with taxes and fees

Located in Denver, this vacation home is in the mountains, a 5-minute drive from East Branch Delaware River and 8 minutes from Pakatakan Farmers' Market.

Hot Tub

Kitchen

Lakefront Luxe Retreat | Beach, Pools, Pickleball

Athens NY

Located in Athens, this vacation home is on the waterfront, a 1-minute drive from Sleepy Hollow Lake and 8 minutes from Hudson River.

Kitchen

Washer

Charming Catskill getaway walking distance to Main St. Pet-friendly!

Catskill NY

With a stay at this vacation home in Catskill, you'll be a 5-minute walk from Thomas Cole National Historic Site and 7 minutes by foot from Greene County Council on the Arts.

Kitchen

Washer

Beautiful, Tranquil Woodstock Mountain House in the Middle of 4 Wooded Acres

Woodstock NY

Located in Woodstock, this vacation home is in a rural location, within a 10-minute drive of Colony and Woodstock Music Shop.

Hot Tub

Kitchen

The Cozycraftsman in the Catskills with Hot tub

Palenville NY

With a stay at this vacation home in Palenville, you'll be within a 15-minute drive of Kaaterskill Falls and Vinnie's Farm Market.

Hot Tub

Kitchen

Don't see what you're looking for?

See all available properties in Windham

View all properties

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.