Cottages in Windham

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Cottages in Windham

A log cabin with a deck, outdoor seating, and a view of a forest.

A woman in a black swimsuit stepping out of a pool into a room with wooden ceiling beams, large windows, and wooden lounge chairs.

A cozy cabin interior with a stone fireplace, a wooden ceiling, and a large window with curtains.

A cabin with a deck, large windows, and a mountain backdrop.

1. Hotel Vienna

Windham

$129

$157 total

includes taxes & fees

Oct 1 - Oct 2

A two-story house with a wrap-around porch, a steeply pitched roof, and a small tower-like structure on the roof.

A garden with blooming pink flowers and green grass.

A wooden staircase leading to a second floor, a red sofa with floral cushions, and a wooden floor.

A covered outdoor seating area with wicker chairs and a table, surrounded by white railings and hanging planters.

2. Antique Rose Inn Windham

Windham

$135

$146 total

includes taxes & fees

Sep 23 - Sep 24

A two-story building with a balcony, surrounded by well-maintained lawns and trees.

A compact living space with a kitchen, dining area, and seating.

A kitchen with a central island, a black refrigerator, pendant lights, and a view through large windows.

A view from a room with a glass door onto an outdoor patio. The patio has a metal table and two chairs, a small pumpkin decoration, and a metal fence.

3. The Winwood Condominiums

Windham

$169

$183 total

includes taxes & fees

Sep 23 - Sep 24

A large, two-story house with multiple porches and string lights.

A building with a porch and outdoor seating area.

A grassy field with a wooden structure overhead, possibly a gazebo or pavilion.

A room with a wooden floor, a chair, a lamp, and a view through a window with a decorative frame.

4. Albergo Allegria Hotel

Windham

$174

$188 total

includes taxes & fees

Sep 23 - Sep 24

A rustic stone building with a sign for Windham Mountain Inn, surrounded by autumn foliage.

A bar with wooden chairs, a bar counter, and various bottles and glasses.

A wooden room with a bed, a nightstand with a lamp, and a wall with tree decorations.

5. Jimmy OConnors Windham Mountain Inn

Windham

$134

$144 total

includes taxes & fees

Oct 6 - Oct 7

A motel with a covered porch, neatly arranged lounge chairs, and a well-maintained garden with yellow flowers.

A hotel room with two beds, wooden paneling on the walls, and two framed pictures.

A sign for Cave Mountain Motel with a rustic stone wall and greenery.

A kitchen with wooden cabinets, a refrigerator, and a window overlooking greenery.

6. Cave Mountain Motel

Windham

A wooden cabin with a door, surrounded by greenery and a stone pathway.

A modern bathroom with a stone floor, wooden walls, a glass shower enclosure, and a black countertop.

A spacious living room with a stone fireplace, wooden staircase, and modern furniture.

A bedroom with a large window, a bed, and a view of a forest.

7. The Haüs Windham

Windham

$110

$350 total

includes taxes & fees

Sep 23 - Sep 24

A cozy wooden interior with a sofa, coffee table, and a view of a deck and greenery outside.

A triangular wooden room with a bed and pillows, a window, and a view of a forested hill.

A room with a large window overlooking a balcony with a view of a hilly landscape. There are two chairs with cushions on the balcony.

A wooden cabin with a triangular roof, a wooden door, and a bench outside.

8. Eastwind Windham

Windham

$289

$344 total

includes taxes & fees

Sep 23 - Sep 24

A large, white, multi-story building with a central courtyard, surrounded by lush greenery and a hilly landscape.

A restaurant setting with neatly arranged tables, each with a menu, plates, and glasses.

A modern bathroom with white subway tiles, a glass shower enclosure, a white sink, and a mirror.

Outdoor seating with tables and chairs, a fire pit, and a wooden bridge in a park setting.

9. Wylder Hotel Windham

Windham

$300

$374 total

includes taxes & fees

Sep 24 - Sep 25

An outdoor patio with a wooden deck, a stone table, and a yellow umbrella.

A cozy lounge area with a sofa, armchairs, a coffee table, and a bookshelf.

A modern living room with a large window, a blue sofa, a wooden coffee table, and a rustic wooden wall.

A bar area with wooden stools, a stone wall, and a view of the outdoor seating area.

10. Hunter Lodge, a Bluebird by Lark

Hunter

$145

$179 total

includes taxes & fees

Oct 6 - Oct 7

A white colonial-style building with green shutters, a porch with a swing, and hanging flower baskets.

A covered porch with outdoor seating, a staircase, and potted plants.

A cozy room with a white sofa, a wooden table with a lamp, and a chair with a patterned cushion. There's a reception desk with a computer and a sign that says "Welcome".

A sign for The Colonial Motel with a green and white color scheme, surrounded by lush greenery and flowering trees.

11. The Colonial Motel

Grand Gorge

$99

$109 total

includes taxes & fees

Sep 23 - Sep 24

A vintage car parked in front of a house surrounded by trees.

A park with Adirondack chairs and a table, surrounded by trees.

A lamp post in a grassy area with autumn foliage in the background.

A dining table set with breakfast items, a red mug, and a glass of orange juice.

12. Mountain Treasure B&B

Maplecrest

$166

$179 total

includes taxes & fees

Oct 18 - Oct 19

A two-story building with a large front porch, a chimney, and a balcony.

A swimming pool with lounge chairs and potted plants.

A wooden bed with a floral bedspread, a small table with a vase, and a poster on the wall.

A hotel room with two beds, a desk, a chair, and a TV on a stand.

13. Moore's Motel

Prattsville

$120

$130 total

includes taxes & fees

Sep 23 - Sep 24

A two-story cabin with a front porch, a chimney, and a deck with outdoor seating.

A large hotel with multiple floors, a parking lot, and a mountainous backdrop.

A cozy lounge area with leather sofas, a fireplace, and a large window overlooking a garden.

A multi-story hotel with a swimming pool, balconies, and outdoor seating areas.

14. Kaatskill Mountain Club & Condos by Vail Resorts

Hunter

$198

$235 total

includes taxes & fees

Sep 24 - Sep 25

A two-story building with a balcony, a porch with a swing, and a small front yard.

A room with two beds, wooden headboards, a red accent wall, and wooden flooring.

A large tree in a grassy area with a small white building in the background.

A park with picnic tables and chairs, a tall cylindrical structure, and autumn-colored trees.

15. SunView Motel

Tannersville

$118

$128 total

includes taxes & fees

Oct 1 - Oct 2

A large, two-story house with a prominent chimney, surrounded by lush greenery and a well-maintained lawn.

A wooden-paneled bedroom with a bed, bedside tables, and a hanging light fixture.

A wooden deck with a table and chairs, a glass door leading to a room with a dresser and a lamp.

A modern hotel lobby with a wooden floor, a reception desk, two patterned armchairs, a chandelier, and a view of the outdoors through a glass door.

16. Hotel Mountain Brook

Tannersville

$204

$220 total

includes taxes & fees

Sep 30 - Oct 1

A two-story building with a porch, a balcony, and a small front yard.

A staircase leading to a room with a stone floor, a potted plant, and a wooden chair.

A room with a view of a landscape through a window, a chair, a table with a laptop, and a bed with books on it.

A spacious living area with a wooden floor, leather sofas, and a dining table.

17. The Perch Hotel

East Windham

$208

$225 total

includes taxes & fees

Sep 24 - Sep 25

A wooden sign for Black Bea Lodge with a green roof building in the background.

Two white Adirondack chairs in a forest with fallen leaves.

A compact hotel room with a wooden floor, a bed with white bedding, a small desk with a microwave, a refrigerator, a wooden nightstand with a lamp, and two floral wall art pieces.

A wooden sign for Black Bear Lodge with a phone number.

18. Black Bear Lodge

Prattsville

$149

$161 total

includes taxes & fees

Sep 23 - Sep 24

A two-story building with a dark exterior and a sloped roof, surrounded by trees and a gravel driveway.

A reception desk with a mirror, potted plants, a welcome sign, and a bench with patterned cushions.

A covered outdoor seating area with picnic tables and umbrellas, surrounded by a forest.

A modern kitchen with dark cabinets, a brick backsplash, and a central island.

19. Starlite Motel

Big Indian

$125

$140 total

includes taxes & fees

Sep 23 - Sep 24

A modern house with a sloped roof, large windows, and a well-maintained lawn.

A modern interior with a wooden dining table, chairs, a sofa, and a bar area with wine bottles.

A bed with white linens and a woven pillow, a window with a view of trees and a wooden structure, and a wall-mounted light fixture.

A spacious living area with a high ceiling, wooden beams, and large windows. There are multiple seating arrangements including a sofa, chairs, and a dining table.

20. AutoCamp Catskills

Saugerties

$144

$200 total

includes taxes & fees

Oct 22 - Oct 23

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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.

Find out more about Windham

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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