A canoe on a calm lake with a forested shoreline.

Vacation homes in Windham

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Vacation homes in Windham

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a vacation rental stay in Windham on Hotels.com. These Windham vacation rentals consistently deliver on quality, location and traveler experience. Last updated on September 12, 2026.

A dining area with a wooden table and chairs, a chandelier, and a view of the outdoors.

A snow-covered outdoor area with a wooden pergola structure.

A cozy living room with a sofa, a dining table, and a fireplace.

A kitchen with wooden cabinets, a large island with stools, a refrigerator, a stove, and a trash can.

1. 3 Mi to Windham Mountain: Pet-friendly Apt w/ Yard

Hensonville

A covered outdoor seating area with a fire feature and benches.

A spacious living area with a dining table, a sofa, and a kitchen with white cabinets and a ceiling fan.

A living room with a blue sofa, a fireplace, and a ceiling fan.

A bedroom with a bed, two bedside tables, a nightstand, a heater, and two windows.

2. Catskills Home, 5 Mins to Windham Mtn Resort!

Windham

A wooden deck with a table, chairs, and a bench.

A cozy living room with a fireplace, a sofa, a coffee table, and a television.

A hallway with a wooden staircase, a wall-mounted lamp, and a door with a dark frame.

A spacious living area with a sofa, coffee table, and a staircase leading to an upper level.

3. Your Windham Fall and Winter Escape Awaits!

Hensonville

4. Windham NY Escape

Hensonville

CNY2,880

CNY3,640 total

includes taxes & fees

Sep 13 - Sep 14

A wooden cabin with large windows, a ceiling fan, a desk, and a chair.

A wooden cabin interior with a ceiling fan, large windows, a sofa, a desk, and a chair.

A cozy room with a wooden ceiling, a gray sofa, a dining table with chairs, and a large window with blinds.

A cozy room with a gray sofa, a patterned bean bag, a small table with a potted plant, and a window with a view of greenery.

5. Pet-friendly Catskills Retreat: Fire Pit & Deck!

Grand Gorge

A two-story house with a front porch, a wooden deck, and a small staircase leading to the entrance.

A living room with a TV, a glass coffee table, a sofa, and a dining area with chairs.

A living room with a sofa, armchair, and coffee table, a dining area with chairs, and a kitchen in the background.

A two-story building with a balcony on the second floor, a covered porch on the first floor, and a wooden deck leading to the entrance.

6. Cozy Catskill Condo - 2 Mi to Windham Mountain Ski

Windham

A rustic barn interior with a sofa set, gas cylinders, and metal stools.

A modern kitchen with wooden cabinets, a central island, and built-in shelves.

A modern living room with a blue sofa, a ceiling fan, and a kitchen area in the background.

A spacious living room with a large sectional sofa, a leather armchair, and a small side table. A ceiling fan is visible, and there is a large window providing natural light.

7. Cozy Catskills Cabin - 12 Mi to Windham Mountain!

East Durham

A dining area with a wooden table, chairs, a chandelier, and a view through a large window.

A wooden deck with snow-covered ground, a round table, and two Adirondack chairs.

A single-story house with a deck, surrounded by snow and trees.

8. Private 7-acre Retreat: On-site Pond, Streams

Jewett

A wooden deck with a grill and a staircase leading to a cabin.

A room with a sofa, bunk bed, desk, chair, and curtains.

A small cabin with a red roof, surrounded by trees and a grassy yard.

A spacious living room with a large window, a fireplace, and a kitchen in the background.

9. Catskill Mtn Home w/ Deck ~ 1 Miles to Zoom Flume!

Cornwallville

A stone fire pit with a plate of food and marshmallows, surrounded by wooden benches and a picnic table.

A kitchen with a central island, stainless steel appliances, and hanging pots.

A two-story house with a porch, a garage, and a stone chimney.

A cozy living room with a stone fireplace, large windows, and comfortable seating.

10. Catskill Park Farm by Avantstay Huge Yard, Fire Pit Near Windham Ski Resort

Ashland

A spacious living room with a fireplace, red sofas, a TV mounted on a brick wall, and a wooden staircase.

A covered deck with a blue building, a gray sofa, a red umbrella, and a barbecue grill.

A spacious living area with a wooden staircase, a red armchair, a beige sofa, and a coffee table.

11. Ski, Hike & Golf: Pet-friendly Windham Retreat

Windham

A building with a front door, a window, and a porch.

A kitchen with wooden cabinets, stainless steel appliances, and a red door.

A spacious living area with a staircase, a sofa, a coffee table, and a kitchen area with a refrigerator and a dining table.

A living room with a sofa, ottoman, and a coffee table. There is a kitchen area with cabinets and a microwave in the background.

12. 1/2 Mi to Windham Mtn: Main Street Condo

Windham

A swimming pool with lounge chairs and a table, surrounded by a fence, with a view of a lake and mountains in the background.

A cozy living room with two sofas, a fireplace, and a large window with a view of trees.

A hot tub with a view of a mountain and autumn trees.

A kitchen with a wooden ceiling, a large window, and a view of a dining area.

13. Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

Hensonville

A spacious room with wooden flooring, a staircase with a wooden railing, and a large window providing natural light.

A porch with four black chairs, a table, and string lights.

A two-story house with a front porch, surrounded by a grassy yard and trees.

A kitchen with a built-in microwave, stove, sink, and dishwasher. There is a window with a view of trees outside.

14. Family Home w/ Yard & Fire Pit in Middleburgh!

Middleburgh

A spacious living area with a red sofa, a glass coffee table, and a wooden ceiling.

A cozy cabin interior with a wooden dining area, a kitchen with a stainless steel refrigerator, and a large window providing a view of the outdoors.

A wooden cabin with a porch, a fireplace, and a view of the surrounding forest.

A wooden cabin bedroom with a bed, bedside tables, and a window with a view of trees.

15. High Peak Heaven: Cozy Log Cabin on 1 Acre!

Hensonville

A modern living room with a black leather sofa, a round coffee table, and a flat-screen TV.

A modern kitchen with white cabinetry, wooden countertops, and a central island.

A modern living room with a flat-screen TV, a grey sofa, two black leather chairs, a white console table, and a small round table with a plant.

A dining area with a round table, six chairs, a ceiling fan, and a window with blinds.

16. 2 Mi to Windham Mountain: Scenic Home w/ Fire Pit!

Windham

A spacious cabin with a large living area, a kitchen, and a dining area.

A wooden cabin interior with a kitchen, dining area, and large windows.

A kitchen with wooden cabinets, a stainless steel refrigerator, and a window with curtains.

A two-story log cabin with a balcony, surrounded by a well-maintained lawn and trees.

17. Grand Windham Retreat w/ Fire Pit & Game Room

Windham

A modern kitchen with stainless steel appliances, wooden beams, and a checkered floor.

A log cabin bedroom with a bed, two bedside tables, a chair, a desk, and a ceiling fan.

A rustic cabin with a fire pit and benches in a forest setting.

A cozy log cabin interior with a plaid sofa, a fireplace, and a stone wall.

18. Pet-friendly New York Cabin w/ Hot Tub & Game Room

Maplecrest

A two-story house with a swimming pool, surrounded by autumn foliage.

A bar area with wooden bar stools, a long counter, and hanging pendant lights.

A bedroom with two beds, wooden walls, large windows with snowy views, and a carpeted floor.

A wooden deck with a picnic table set for a meal, surrounded by trees and a mountainous backdrop.

19. Secluded Catskills Retreat Heated Pool Hot Tub Game Rooms The Hilltop Hideaway by Avantstay

Hunter

A wooden deck with a grill, overlooking a forested area with autumn foliage.

20. Catskills Basecamp Near Hunter Mountain

Jewett

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Top landmarks in Windham

Windham Mountain Resort

9.0/10 (313 reviews)

Skiers and snowboarders might want to test out the slopes at Windham Mountain Resort, a skiing spot located 1.2 mi (1.9 km) from central Windham. If you master the slopes, Hunter Mountain and Mountain Trails Cross Country Ski and Snowshoe Center are also just a short drive away.

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Windham Country Club

8.4/10 (20 reviews)

You might want to practice your swing at Windham Country Club, a golf course located 1 mi (1.6 km) from central Windham.

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Windham Vineyards and Winery

9.0/10 (15 reviews)

Travelers might want a tour of Windham Vineyards and Winery, just one of the places to visit, and located 3.4 mi (5.4 km) from central Windham.

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Huntersfield State Forest

Huntersfield State Forest is 6.2 mi (9.9 km) from central Windham, why not stop by during your stay.

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Elm Ridge Wild Forest

Elm Ridge Wild Forest is 3.5 mi (5.7 km) from central Windham, why not stop by during your stay.

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Ashland Park

Ashland Park is 4.4 mi (7 km) from central Windham, why not stop by during your stay.

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Learn more about Windham

Tucked into the Catskills, this mountain hamlet transforms with the seasons. Carve fresh powder at Windham Mountain Resort in winter, where the slopes welcome skiers of all abilities. Summer brings hikers to scenic trails throughout Catskill State Park, with panoramic vistas worth every uphill step. The Windham Country Club offers 18 challenging holes for golfers seeking mountain backdrops with their birdies. After outdoor adventures, explore the quaint downtown where coffeehouses serve perfect post-adventure refreshments. Wine enthusiasts can sample local vintages at Windham Vineyards and Winery. For additional outdoor pursuits, nearby Hunter Mountain provides more terrain to explore, while Huntersfield State Forest offers quieter woodland escapes away from the resort crowds.

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A wooden covered bridge in a forest with autumn foliage.

About the destination

Windham is a relaxing city where you can spend time checking out its coffee shops. If you're visiting during colder months, enjoy activities such as skiing during your stay. Plan a fun excursion to Windham Country Club and Windham Vineyards and Winery while here. There's plenty more to see, including sights like Windham Mountain Resort and Catskill State Park.

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