Windham Guest Houses

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

Check dates for Windham hotels

Guest Houses in Windham

The Herwood Inn

148 Tinker St Woodstock NY

$176 nightly

$197 total

Dec 10 - Dec 11

Total with taxes and fees

When you a stay at The Herwood Inn in Woodstock, you'll be in the mountains, just steps from Catskill State Park and The Comeau Property.

Hot Tub

Pet friendly

Shadowcrest

973 Main St Fleischmanns NY

$145 nightly

$160 total

Dec 8 - Dec 9

Total with taxes and fees

Located in Fleischmanns, Shadowcrest is in a regional park, a 5-minute drive from Belleayre Mountain Ski Center and 6 minutes from Pine Hill Community Center.

Breakfast included

Pet friendly

The Old Catskill Game Farm Inn

400 Game Farm Rd Catskill NY

With a stay at The Old Catskill Game Farm Inn in Catskill, you'll be 11.3 mi (18.2 km) from Greene County Council on the Arts and 11.9 mi (19.2 km) from Thomas Cole National Historic Site.

Pet friendly

Parking included

Beds on Clouds

5320 Main Street Windham NY

$189 nightly

$204 total

Dec 8 - Dec 9

Total with taxes and fees

With a stay at Beds on Clouds in Windham, you'll be near ski lifts, within a 5-minute drive of Windham Mountain Resort and Catskill State Park.

Parking included

Free WiFi

The Woodbine Inn

144 Malden Ave Palenville NY

Located in Palenville, The Woodbine Inn is in the mountains, a 1-minute drive from Catskill State Park and 6 minutes from Vinnie's Farm Market.

Pet friendly

Parking included

Catskills Hideaway w/ Sauna Minutes from Hiking

Mount Tremper NY

With a stay at this guesthouse in Mount Tremper, you'll be within a 10-minute drive of Catskill Mountains and Catskill State Park.

Pet friendly

Air conditioning

LEEDS A GREAT ESCAPE

Leeds NY

Located in Catskill, this guesthouse is in a rural location, a 5-minute drive from Catskill Golf Club and 5 minutes from Thomas Cole National Historic Site.

Air conditioning

Parking available

Gateway Lodge Bed & Breakfast

11 Highlands Road Highmount NY

With a stay at Gateway Lodge Bed & Breakfast in Highmount, you'll be a 2-minute drive from Belleayre Mountain Ski Center and 7 minutes from Catskill Mountains.

Pet friendly

Parking included

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.