Hotels in Windham

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Where to stay in Windham?

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

A wooden covered bridge in a forested area with a paved path leading to it.

A cozy cabin interior with a stone fireplace, wooden walls, a dining area with a red and black checkered tablecloth, and a television mounted above the fireplace.

A modern building with large glass doors, a staircase leading up to the entrance, and a potted plant beside the door.

1. Hotel Vienna

Windham

$129

$157 total

includes taxes & fees

Sep 13 - Sep 14

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

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.

A building with a porch and outdoor seating area.

2. Albergo Allegria Hotel

Windham

$174

$188 total

includes taxes & fees

Sep 13 - Sep 14

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

A pool table with balls and a cue stick.

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.

3. Jimmy OConnors Windham Mountain Inn

Windham

$134

$144 total

includes taxes & fees

Oct 6 - Oct 7

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

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.

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

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

4. The Winwood Condominiums

Windham

$169

$183 total

includes taxes & fees

Sep 13 - Sep 14

A two-story house with a stone chimney, a porch with flower boxes, and a well-maintained lawn.

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

A white door with a sign reading "BREAKFAST" above it, a thermometer, and a drawing of stacked cups with steam.

A grassy field with a bench and a mountain in the background.

5. Cave Mountain Motel

Windham

$139

$150 total

includes taxes & fees

Oct 1 - Oct 2

A large, multi-story house with a wrap-around porch and a small tower-like structure on the roof.

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.

A dining room with a wooden table, chairs, a chandelier, and a vase of flowers.

6. Antique Rose Inn Windham

Windham

$135

$146 total

includes taxes & fees

Sep 14 - Sep 15

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

A bar area with wooden beams, a bar counter, and four bar stools.

A wooden cabin with a balcony, surrounded by snow-covered trees.

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

7. Eastwind Windham

Windham

$289

$344 total

includes taxes & fees

Sep 13 - Sep 14

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 room with two blue armchairs, a small round table, a lamp, and a large window with curtains.

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

8. Wylder Hotel Windham

Windham

$300

$374 total

includes taxes & fees

Sep 24 - Sep 25

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

A modern bedroom with a large bed, a view of greenery through floor-to-ceiling windows, and a wooden ceiling.

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

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

9. The Haüs Windham

Windham

$135

$295 total

includes taxes & fees

Sep 30 - Oct 1

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

A circular fire pit with chairs around it, set on a grassy area with a wooden fence and trees in the background.

A bedroom with a large window offering a view of a forested mountain.

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

10. Hunter Lodge, a Bluebird by Lark

Hunter

$135

$168 total

includes taxes & fees

Sep 20 - Sep 21

A swimming pool with lounge chairs and potted plants.

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

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

A two-story motel with a central staircase, balconies, and a grassy front yard.

11. Moore's Motel

Prattsville

$120

$130 total

includes taxes & fees

Sep 11 - Sep 12

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.

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

A chair with a blanket, a potted plant, and a view of a snowy landscape through a glass door.

12. The Perch Hotel

East Windham

$208

$225 total

includes taxes & fees

Sep 17 - Sep 18

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

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

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

A well-lit hallway with a wooden staircase, a decorative vase, and a dining area with a table and chairs.

13. Mountain Treasure B&B

Maplecrest

$169

$183 total

includes taxes & fees

Sep 13 - Sep 14

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 bedroom with a fireplace, a wooden ceiling, and a view of the outdoors.

14. Hotel Mountain Brook

Tannersville

$175

$189 total

includes taxes & fees

Sep 14 - Sep 15

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

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

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

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".

15. The Colonial Motel

Grand Gorge

$99

$109 total

includes taxes & fees

Sep 13 - Sep 14

A multi-story building with outdoor seating and a stone-paved patio.

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

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

A cozy cabin interior with a wooden ceiling, two sofas, a coffee table, a fireplace, and a television.

16. Kaatskill Mountain Club & Condos by Vail Resorts

Hunter

$198

$235 total

includes taxes & fees

Sep 28 - Sep 29

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

A bathroom with three sinks, a trash can, and a chair.

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

A hallway with a wooden door leading to a bathroom, a blue couch with a cushion, and a kitchen area with cabinets and a sink.

17. SunView Motel

Tannersville

$118

$128 total

includes taxes & fees

Oct 1 - Oct 2

A river flowing through a forested area with rocks and autumn-colored trees.

A front door with a WiFi sign, a Christmas wreath, and a bear statue.

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

Two white Adirondack chairs in a forest with fallen leaves.

18. Black Bear Lodge

Prattsville

$149

$161 total

includes taxes & fees

Sep 13 - Sep 14

A large, multi-story house with a prominent tower, surrounded by a well-maintained lawn and trees.

A richly decorated living room with a sofa, a coffee table, and a colorful stained glass lamp.

A dining area with wooden furniture, a stained glass window, and a cabinet with glass doors.

A pathway lined with trees and illuminated string lights, leading to a building with a visible entrance.

19. Fairlawn Inn

Hunter

$259

$280 total

includes taxes & fees

Sep 20 - Sep 21

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.

A modern house with a large garage and a vintage camper parked in the driveway.

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

20. AutoCamp Catskills

Saugerties

$144

$200 total

includes taxes & fees

Oct 8 - Oct 9

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Go beyond your typical stay in Windham

Pool

Apartment

Cottage

Pet friendly

Family friendly

Our prices for hotels in Windham are cheapest in September

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.

See all hotels in Windham

A wooden covered bridge in a forest with autumn foliage.

Check out reviews of Windham hotels guests love

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

10/10 Excellent

"Great hotel, very clean very helpful staff. Water pressure in shower in second floor was not good"

Hunter Lodge, a Bluebird by Lark

10/10 Excellent

"This was an extremely delightful stay for end of summer! Great setting with beautiful grounds, easy to get anywhere in Hunter and all the other nearby towns. Stayed in a King loft which was great, lots of room to relax, very clean and well maintained. It was very handy to have a mini-fridge and microwave, but also enjoyed dinner downstairs at the Tavern. The complementary breakfast hit just right before hitting the road for the day."

Kaatskill Mountain Club & Condos by Vail Resorts

10/10 Excellent

"It was a wonderful hotel. Although it had gotten quite chilly, the pool was heated and there was also a hot tub, so the kids really enjoyed swimming and relaxing in the pool after our trek. Since it was the off-season, the hotel was quiet and not crowded. The restaurant was excellent, with great service and delicious food that truly impressed us. All of the staff were friendly and helpful, and we appreciated how well the property was maintained. We had a really enjoyable stay and would love to come back during the ski season next time!"

Urban Cowboy Lodge

8/10 Good

"The property and stay was great. The reason for four stars vs. five were the expectations. The descriptions and their Instagram oversells the place so you go expecting more. A little more transparency and marketing the property for its true self - it's a fantastic spot."

Jimmy OConnors Windham Mountain Inn

10/10 Excellent

"Jimmy Conner Inn is truly one of the best places to stay if you’re looking for somewhere quiet, peaceful, and surrounded by nature. Everything is so convenient you have a bar and restaurant right on the property, so you don’t even need to leave. It’s incredibly peaceful and the perfect place to decompress from all the noise and craziness of the city. The service was excellent, and the whole experience made us feel so welcomed and taken care of. They even have a beautiful fire pit where you can relax and enjoy the evening. Highly recommend this place if you’re looking to disconnect, reconnect with nature, and just enjoy some peace and quiet! 🔥🌲"

AutoCamp Catskills

10/10 Excellent

"Over all everything is good"

Hotel Vienna

10/10 Excellent

"We vacationed and traveled for 11 days and stayed at 10 different hotels in upstate NY. This hotel was the BEST. It was spacious, very clean, with an excellent breakfast. The host was polite, professional, and a lot of fun to visit with. We found an excellent place to wrap up with our sightseeing adventure. You will not be disappointed!!"

The Winwood Condominiums

10/10 Excellent

"Clean room with nice couch plus kitchenette. Enjoyed setting on patio. Great location, easy walk into town with several restaurants."

Eastwind Windham

10/10 Excellent

"The staff was friendly and the room was clean and comfortable. Would love to come back again!"

Frequently asked questions

What accommodations do travelers like in Windham?

Guests like Hotel Vienna, Wylder Hotel Windham and Eastwind Windham.

Can I book refundable accommodations in Windham?

If you're looking for the flexibility to change your plans to Windham, most properties offer refundable* rates you can book. You can find these properties by searching our site and using the "fully refundable" filter to narrow the results down.

Where should I stay in Windham if I'm looking for a cheap accommodation?

The Haüs Windham is an accommodation you might want to consider that'll save you money.

Where can I stay in Windham if I want a vacation rental instead of a hotel?

If you're looking for a good alternative to a hotel, review our selection of 139 vacation homes. In addition, there are 19 apartments and 32 condos.

What will the weather in Windham be like during my vacation?

The warmest months in Windham are usually July and August with an average temp of 65°F. January and February are the chilliest months when the average temp is 27°F. The rainiest months are July and August.

Why should I book my Windham hotel with Hotels.com?

There are plenty of reasons to book your Windham travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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Book Hotels in Windham on Hotels.com

Hotels in Windham

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Where to stay in Windham?

1. Hotel Vienna

2. Albergo Allegria Hotel

3. Jimmy OConnors Windham Mountain Inn

4. The Winwood Condominiums

5. Cave Mountain Motel

6. Antique Rose Inn Windham

7. Eastwind Windham

8. Wylder Hotel Windham

9. The Haüs Windham

10. Hunter Lodge, a Bluebird by Lark

11. Moore's Motel

12. The Perch Hotel

13. Mountain Treasure B&B

14. Hotel Mountain Brook

15. The Colonial Motel

16. Kaatskill Mountain Club & Condos by Vail Resorts

17. SunView Motel

18. Black Bear Lodge

19. Fairlawn Inn

20. AutoCamp Catskills

Go beyond your typical stay in Windham

Price trends for hotels in Windham

Typical weather for Windham

Top landmarks in Windham

Windham Mountain Resort

Windham Country Club

Windham Vineyards and Winery

Huntersfield State Forest

Elm Ridge Wild Forest

Ashland Park

Learn more about Windham

Check out reviews of Windham hotels guests love

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

Hunter Lodge, a Bluebird by Lark

Kaatskill Mountain Club & Condos by Vail Resorts

Urban Cowboy Lodge

Jimmy OConnors Windham Mountain Inn

AutoCamp Catskills

Hotel Vienna

The Winwood Condominiums

Eastwind Windham

Frequently asked questions

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