Town
Where to Stay in Windham
Windham is a ski town with restaurants and hotels that draw visitors in every season. Windham Mountain Club has 60 trails and a 1,600-foot vertical drop, and much of the lodging around it has opened or been renovated since the 2010s. The lodging on Route 23 covers a range of budgets and styles: Eastwind Hotel & Bar, a 1920s-era lodge redesigned in a Scandinavian modernist style; Union + Post next door; Hotel Vienna, with an indoor pool; Wylder Windham, on 20 acres along the Batavia Kill; and Albergo Allegria, open since 1982. Matilda, at The Henson in nearby Hensonville, comes from the chefs behind Wildair and Bar Contra in New York City. Main Street has an independent bookshop and specialty food shops, and the Windham Path is a 1.5-mile walk through meadows along the Batavia Kill.
Eastwind Hotel & Bar
Featured StayWindham, NY · Boutique Hotel
A hotel on Route 23 in Windham, in a 1920s-era lodge redesigned in a Scandinavian modernist style, with 23 rooms and 10 Lushna cabins. The cabins range from 150-square-foot A-frames to 400-square-foot suites with kitchenettes. A breakfast basket is delivered daily on request, and Dandies is the restaurant and bar. Listed in the MICHELIN Guide.
Lushna cabins from 150-square-foot A-frames to suites with kitchenettes. A breakfast basket delivered daily on request. Listed in the MICHELIN Guide.
Wylder Windham
Windham, NY · Resort
A hotel on 20 acres along the Batavia Kill in Windham, with seven kinds of lodging in buildings that range from Victorian houses to historic lodges. There is a heated pool, wood-fired saunas, an indoor recreation room, pickleball courts, lawn games, fire pits and electric bikes, and guests can tube on the river. Babblers café serves breakfast, lunch and dinner, and the property has a dog run.
Union + Post
Windham, NY · Boutique Motel
A 12-room hotel on Route 23 in Windham, next door to Eastwind, with a 5-bedroom hilltop house for groups. The restaurant serves New American food made with ingredients from local farms, and has the building's original hickory-wrapped bar, a second-floor library and an outdoor deck. Rooms range from standard kings to 1- and 2-bedroom suites.
Albergo Allegria Hotel
Windham, NY · Boutique Hotel
A hotel at 43 Route 296 in Windham, open since 1982, whose name is Italian for 'Inn of Happiness.' Rooms come in three categories, and The Cottage on Main Street is rented separately. Food and beverage service has been suspended since December 2025 while the chef is on sabbatical, so there is no breakfast or dinner on site. Windham Mountain is a short drive.
Hotel Vienna
Windham, NY · Boutique Hotel
A 29-room lodge on more than 9 acres at 107 Route 296 in Windham, with a heated indoor pool, a wood barrel sauna and direct access to the Windham Path. Continental breakfast is included, mountain-view rooms have private balconies, and housekeeping is daily. A separate 4-bedroom cabin sleeps up to 12 and has its own hot tub, grill and fire pit. The decor is modern European, not alpine.
Windham Mountain Club
Windham · Resort
Lodging at Windham Mountain Club, the ski area in Windham with 60 trails and 12 lifts. The Outpost has 20 rooms, and stays include access to the club's restaurants, spa, gym and golf course. Outpost guests can buy lift tickets even on sold-out days. In summer the club offers golf, mountain e-biking, fly fishing, sporting clays and guided hikes.
Why Stay in Windham
- •Windham Mountain Club has 60 trails, a 1,600-foot vertical drop and terrain parks, and since 2023 it has limited the day tickets it sells to the public.
- •Matilda at The Henson, in Hensonville, draws diners from well beyond the area, and Main Street has other restaurants.
- •A walkable main street with actual independent retail: Briars & Brambles Books, Paracasa specialty foods, Catskill Mountain Country Store.
- •Year-round programming at Windham Mountain Club: mountain biking, fly fishing, hiking, and golf in the off-season.
What Makes This Area Interesting
- •Windham Mountain Club: 60 trails and a 1,600-foot vertical drop; most properties here are 5 to 20 minutes away.
- •Kaaterskill Clove: the drive east from Tannersville to Palenville on Route 23A is a well-known foliage drive.
- •Mountain Top Arboretum: 178 free acres above 3,000 feet, open to the public year-round.
- •Hunter Mountain: about 20 minutes south via Route 296; more terrain for a multi-mountain trip.
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