Find hotels in Windham, NY from SARĀ 336

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Our top choices for Windham hotels

Hotel Vienna

Hotel Vienna
3.0 star property
Windham
9.4 out of 10, Exceptional, (731)
"Great service, nice and clean hotel."
United States
Mary
Hotel Vienna

Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
8.6 out of 10, Excellent, (89)
"Spotless room and great staff "
United States
Josue
The price is SARĀ 942
SARĀ 1,205 total
includes taxes & fees
30 Dec - 31 Dec
Wylder Hotel Windham

Winwood Condominiums by Windham Mountain Club

Winwood Condominiums by Windham Mountain Club
3.0 star property
Windham
8.8 out of 10, Excellent, (344)
"convenient nice and clean residence with kitchen and market nearby."
United States
Jatin
The price is SARĀ 709
SARĀ 766 total
includes taxes & fees
4 Jan - 5 January 2026
Winwood Condominiums by Windham Mountain Club

Eastwind Windham

Eastwind Windham
2.0 star property
Windham
9.4 out of 10, Exceptional, (76)
"I loved our stay!"
United States
Erika
The price is SARĀ 1,061
SARĀ 1,264 total
includes taxes & fees
30 Dec - 31 Dec
Eastwind Windham

Antique Rose Inn Windham

Antique Rose Inn Windham
3.0 star property
Windham
9.0 out of 10, Wonderful, (125)
"Very entertaining owner, comfortable bed, quiet at night, bathroom shareable with the other two rooms, all very clean and cure for details. Great breakfast, not very far from Windham. "
United States
Simona
The price is SARĀ 506
SARĀ 547 total
includes taxes & fees
5 Jan - 6 January 2026
Antique Rose Inn Windham

Albergo Allegria Hotel & Breakfast Restaurant

Albergo Allegria Hotel & Breakfast Restaurant
3.5 star property
Windham
9.6 out of 10, Exceptional, (270)
"Nice people and great breakfast. "
United States
Remelin
The price is SARĀ 502
SARĀ 542 total
includes taxes & fees
4 Jan - 5 January 2026
Albergo Allegria Hotel & Breakfast Restaurant

The Outpost by Windham Mountain Club

The Outpost by Windham Mountain Club
2.5 star property
Windham
8.6 out of 10, Excellent, (4)
"Cozy and warm. I think it would be better to visit during the winter season"
United States
TAEJUN
The price is SARĀ 938
SARĀ 1,013 total
includes taxes & fees
1 Jan - 2 January 2026
The Outpost by Windham Mountain Club

The Haüs Windham

The Haüs Windham
2.0 star property
Windham
8.6 out of 10, Excellent, (19)
"Very good"
United States
Sophia
The price is SARĀ 732
SARĀ 1,094 total
includes taxes & fees
7 Jan - 8 January 2026
The Haüs Windham

Beds on Clouds

Beds on Clouds
3.0 star property
Windham
7.4 out of 10, Good, (68)
"Great spot for a weekend getaway"
United States
Bertrand
The price is SARĀ 707
SARĀ 764 total
includes taxes & fees
5 Jan - 6 January 2026
Beds on Clouds

Cave Mountain Motel

Cave Mountain Motel
2.5 star property
Windham
9.4 out of 10, Exceptional, (135)
"I enjoyed my stay here. I found the owner to have a good sense of humor. They have a light breakfast and coffee available. The room had everything I needed to have a comfortable stay. Check in went smoothly."
United States
Alexander
The price is SARĀ 521
SARĀ 563 total
includes taxes & fees
30 Dec - 31 Dec
Cave Mountain Motel

The Perch Hotel

The Perch Hotel
2.0 star property
Cornwallville
9.4 out of 10, Exceptional, (22)
"Lovely stay"
United States
Barry
The price is SARĀ 1,482
SARĀ 1,601 total
includes taxes & fees
10 Jan - 11 January 2026
The Perch Hotel

The Herwood Inn

The Herwood Inn
4.5 star property
Woodstock
9.8 out of 10, Exceptional, (93)
"Quaint, quirky, very environmentally conscious, fun old vinyls, and a cedar fragrant hot tub!"
United States
Dietlinde
The price is SARĀ 633
SARĀ 709 total
includes taxes & fees
13 Jan - 14 January 2026
The Herwood Inn

Twin Gables of Woodstock

Twin Gables of Woodstock
3.0 star property
Woodstock
9.8 out of 10, Exceptional, (193)
"Amazing stay!!! Super hippie vibe and lived every minute of it. "
United States
Heather
The price is SARĀ 484
SARĀ 542 total
includes taxes & fees
4 Jan - 5 January 2026
Twin Gables of Woodstock

Woodstock Way Hotel

Woodstock Way Hotel
4.0 star property
Woodstock
9.6 out of 10, Exceptional, (217)
"The room and views were lovely, and we loved the Tannery cafe!"
United States
Katherine
Woodstock Way Hotel

Morning Glory B n B Woodstock NY

Morning Glory B n B Woodstock NY
3.0 star property
Woodstock
8.4 out of 10, Very Good, (155)
"Close to village and convenient to walk around Woodstock"
United States
Richard
The price is SARĀ 709
SARĀ 794 total
includes taxes & fees
4 Jan - 5 January 2026
Morning Glory B n B Woodstock NY

The Woodstock Inn on the Millstream

The Woodstock Inn on the Millstream
3.0 star property
Woodstock
9.0 out of 10, Wonderful, (204)
"Clean room and friendly staff. We appreciated the little happy hour snacks and the breakfast was more than we imagined!"
United States
Amber
The price is SARĀ 671
SARĀ 752 total
includes taxes & fees
1 Jan - 2 January 2026
The Woodstock Inn on the Millstream

Black Bear Lodge

Black Bear Lodge
2.5 star property
Prattsville
9.0 out of 10, Wonderful, (131)
"A great place to stay in the Catskills at a reasonable price point. "
United States
Peter
The price is SARĀ 559
SARĀ 604 total
includes taxes & fees
4 Jan - 5 January 2026
Black Bear Lodge

The Colonial Motel

The Colonial Motel
2.5 star property
Grand Gorge
9.4 out of 10, Exceptional, (407)
"Comfortable, quiet and good value vs other options in the region. "
United States
Karl
The price is SARĀ 334
SARĀ 368 total
includes taxes & fees
30 Dec - 31 Dec
The Colonial Motel

Moore's Motel

Moore's Motel
2.5 star property
Prattsville
8.6 out of 10, Excellent, (158)
"Stay here every time we are in the area. And its always a great stay and a good time down the street at the prattsville tavern. Moores is excellent"
United States
John
The price is SARĀ 450
SARĀ 486 total
includes taxes & fees
1 Jan - 2 January 2026
Moore's Motel

Catskill Seasons Inn

Catskill Seasons Inn
2.5 star property
Shandaken
8.2 out of 10, Very Good, (241)
"Great Stay would definitely recommend "
United States
Jay
The price is SARĀ 559
SARĀ 626 total
includes taxes & fees
4 Jan - 5 January 2026
Catskill Seasons Inn
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.

Great weekend hotel deals inĀ Windham, NY

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Stay near popular Windham attractions

Learn more about Windham

Nestled in the Catskills, this mountain town transforms from a powdery ski paradise to a lush hiking haven with seasons. Visit Windham Mountain for thrilling slopes in winter or explore the scenic Rail Trail when summer's wildflowers frame perfect mountain views.

Amazing foliage upstate New York. Morning sunlight spills over the golden foliage. Windham NY is one of the most popular destination for scenic drives, bike trails, foliage and nature lovers.; Shutter

Top Windham Hotel Reviews

More cheap stays in Windham

Hotels in Windham with star-rating

Find out more about Windham

Top reasons to visit Windham

  • Thrilling Skiing: Experience fantastic skiing opportunities at Windham Mountain, catering to all skill levels.
  • Vibrant Nightlife: Enjoy lively nightlife options that add excitement to your evenings in Windham.
  • Scenic Hiking Trails: Explore breathtaking hiking trails and discover nearby waterfalls and state parks.
  • Charming Local Shops: Indulge in window shopping at delightful local boutiques for unique finds.
  • Hudson Valley Vineyards: Discover local vineyards and enjoy wine tasting in the beautiful Hudson Valley.

Find great hotels in and around Windham

Discover the charm of Windham, New York, with a variety of hotel accommodations designed to meet the needs of every traveler. Whether you're seeking an adventurous getaway, a family-friendly retreat, or a pet-friendly vacation, Windham offers an array of lodging options, including agritourism properties and hotels. Explore the best hotels, read reviews, and find competitive room rates to make your stay unforgettable.

  • Hunter Lodge, a Bluebird by Lark: Embrace adventure and inclusivity at Hunter Lodge, a Bluebird by Lark, located 12.9km from Windham. This hotel is a haven for pet lovers and LGBTQIA travelers, offering a warm, welcoming atmosphere. Enjoy an array of outdoor activities, from snowshoeing and skiing to kayaking and fishing, all just moments away. The property is designed with adventure seekers in mind, and it allows pets with specific amenities like food and water bowls. Experience a unique blend of comfort and camaraderie in a setting that celebrates diversity.
  • Hotel Vienna: Situated in the heart of Windham, Hotel Vienna caters to business travelers and golf enthusiasts alike. This charming hotel offers golf-themed experiences and is close to various recreational activities, including snowboarding, swimming, and biking rentals. With a focus on adventure and professional needs, guests appreciate the well-appointed rooms and convenient access to local attractions. Whether you're here for work or play, Hotel Vienna provides a perfect balance of comfort and functionality.
  • Hotel Mountain Brook: Located 16.1km from Windham, Hotel Mountain Brook is a 4-star retreat that welcomes both adventure seekers and pet owners. This property offers a range of exciting activities, including horseback riding, birdwatching, and skiing. With a pet-friendly policy that includes amenities for furry friends, guests can enjoy the great outdoors without leaving their pets behind. The hotel combines luxury with a rustic charm, making it an ideal spot for those looking to explore the natural beauty of the area.

Where to stay in and around Windham

Windham, New York, offers a perfect blend of adventure and relaxation for travelers. Enjoy skiing in winter or explore local vineyards in the beautiful Hudson Valley. Experience the charming atmosphere of nearby Woodstock, with its friendly vibe and scenic views. Whether you're seeking a fall getaway or a secluded retreat, Windham and its surrounding areas promise unforgettable experiences for families and adventurers alike.

  • Hunter: Nestled 11.3km from Windham, Hunter is a charming city renowned for its outdoor adventures, particularly skiing. The area sees a moderate influx of tourists, peaking from December to February when winter sports enthusiasts flock to its ski resorts and picturesque fields. Beyond skiing, visitors can explore the stunning local landmarks, including breathtaking mountains, serene lakes, and captivating waterfalls. The vibrant community offers various sports experiences that make it a perfect destination for adventure seekers looking to embrace the thrill of the outdoors.
  • Hensonville: Just 3.2km away from Windham, Hensonville is a delightful city that attracts visitors year-round, with a peak in the summer months from June to August. Like its neighboring towns, Hensonville is a hub for skiing and outdoor sports, featuring excellent ski fields and resorts. The surrounding natural beauty, including mountains, lakes, and waterfalls, provides an idyllic backdrop for adventure. Hensonville’s inviting atmosphere and numerous recreational opportunities make it a great choice for those seeking both relaxation and excitement amidst nature.
  • East Windham: Located within the Windham area, East Windham is a quaint village that draws visitors with its outdoor activities and ski resorts. The peak tourist season occurs from July to August and in October, making it an ideal summer getaway. East Windham is perfect for those who love adventure, offering access to ski fields and stunning mountain vistas. Additionally, the village features family-friendly attractions such as a theme park and a waterpark, ensuring a well-rounded experience for travelers of all ages looking to enjoy the great outdoors.

Things to do in and around Windham

Windham, New York, offers a thrilling vacation experience with its fantastic skiing opportunities at local ski resorts. In addition to hitting the slopes, visitors can enjoy the vibrant nightlife, explore the Zoom Flume water park, and discover scenic hiking trails, making it a haven for adventure enthusiasts. Don’t forget to take some time for window shopping in the charming local shops to complete your visit.

Shopping

In Windham, you can visit Vinnie's Farm Market for fresh products and local goods. If you're up for a drive, check out the Woodstock Music Shop for unique music-related gifts, or head to the Hudson Valley Mall for a wider selection of shops and entertainment options.

Recreation

Experience the Windham Country Club for a round of golf amidst beautiful landscapes and a vibrant outdoor atmosphere. For a unique retreat, visit Copperhood Retreat & Spa, where you can indulge in rejuvenating body treatments that emphasize wellness and relaxation, just a short drive from Windham.

Adventure

At Windham Mountain Resort, experience thrilling skiing and snowboarding on pristine slopes. For family fun, visit Zoom Flume waterpark, where you can enjoy exhilarating water rides. Take a scenic ride on the Northern Express Ski Lift for breathtaking views of the snowy landscape.

Nightlife

Experience the vibrant nightlife in Windham by visiting Mount Tremper Arts, located 29.0km away, offering a mix of romance and culture. Colony, 32.2km from Windham, also promises an entertaining evening. For a grander experience, check out the Ulster Performing Arts Center, 46.7km away, showcasing diverse performances.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Windham

To save money on your trip to Windham, plan your visit during the off-peak months of March to April or November, when prices are lower. Tuesdays offer the cheapest accommodation rates, while Fridays are the most expensive. Use Expedia to compare hotel rates and look for vacation packages that combine flights and activities for additional savings. Explore the town on foot to avoid public transport costs, and check for free activities in the area to enhance your experience without overspending.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Windham are March to April and November, where the prices are slightly lower. This is in comparison to July to August and October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Windham is Tuesday. The most expensive day to stay in Windham is Friday.
  • Find cheap hotels on Expedia: Utilize Expedia's search tool to refine your options based on your budget, desired location, and preferred hotel type. To find the best prices and deals, arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your Wyndham hotel reservation with your flights and activities when you book an Expedia package.

Find the best attractions in and around Windham

Windham, New York, is a prime destination for adventure seekers, offering skiing at Windham Mountain and breathtaking views at nearby waterfalls and state parks. Visitors can enjoy outdoor activities while exploring the Windham Mountain Club and immersing themselves in the local culture and scenery. Whether you're looking to hit the slopes or enjoy nature's beauty, Windham promises an unforgettable experience for all types of travelers.

  • Windham Mountain Resort: Experience the thrill of skiing at Windham Mountain Resort, a premier destination for outdoor adventure. Whether you’re a seasoned skier or a beginner, the resort offers diverse slopes and breathtaking views, making it perfect for a winter getaway.
  • Kaaterskill Falls: Discover the enchanting Kaaterskill Falls, a stunning waterfall located 19.3km from Windham. This natural wonder is perfect for romantic hikes and outdoor exploration, surrounded by lush landscapes and breathtaking vistas.
  • Mountain Top Arboretum: Visit the Mountain Top Arboretum, an 12.9km journey from Windham, where families can enjoy peaceful trails and a variety of native plants. This tranquil setting is ideal for picnics and leisurely strolls in nature.

Best time to go to Windham

The best time to visit Windham can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Windham falls in July, when visitor numbers are average and weather is mostly sunny with light rain. The coolest average temperature in Windham falls in January, visitor numbers are slightly high and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January22.1°F (-5.5°C)Light RainMostly CloudySlightly HighAverage
February24.1°F (-4.4°C)Light RainMostly CloudySlightly HighAverage
March31.6°F (-0.2°C)Light RainMostly CloudyAverageSlightly Low
April43.3°F (6.3°C)Light RainMostly CloudyAverageSlightly Low
May55.6°F (13.1°C)Light RainMostly SunnySlightly LowAverage
June63.0°F (17.2°C)Light RainMostly SunnySlightly LowAverage
July68.7°F (20.4°C)Light RainMostly SunnyAverageSlightly High
August66.7°F (19.3°C)Light RainMostly SunnyAverageSlightly High
September59.9°F (15.5°C)Light RainMostly SunnyAverageAverage
October48.9°F (9.4°C)Light RainMostly SunnySlightly LowSlightly High
November36.7°F (2.6°C)Light RainMostly SunnyAverageSlightly Low
December28.8°F (-1.8°C)Light RainMostly CloudySlightly HighAverage

The nearest major airports for your trip to Windham

When planning your visit to Windham, New York, there are several major airports to consider. ALBany International Airport (ALB) is 61.2km away, with nearby hotel options like the 4-star Park Manor Hotel and The Landing Hotel at Rivers Casino & Resort, both 12.9km from the airport. Newburgh's Stewart International Airport (SWF) is 90.1km away, with the 3.5-star Dutchess Inn and Spa at Beacon located 9.7km from SWF. Lastly, Hudson's Columbia County Airport (HCC) is 212.9km away, featuring hotels like The Wick, Hudson, a 4-star property just 8.0km from HCC, offering transfers and shuttles for convenient access.

Frequently asked questions

What's the best place to stay in Windham?
Hotel Vienna is a favorite with Expedia customers. This hotel offers free breakfast and an indoor pool. Reviews from our site also recommend Eastwind Windham and Antique Rose Inn Windham as top choices for your trip. See all available top hotels, or vacation rentals in Windham.
What are some of the best vacation home rentals that Windham has to offer?
A'Neils Windham Ski Lodge & Family Retreat: This highly rated vacation home rental in Windham is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 10 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. Our travelers also rate Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts as a favorite home for rent in Windham. See all vacation rentals in Windham.
If I need to cancel my hotel reservation in Windham, will I receive a refund?
Yes, the majority of hotel bookings are fully refundable if you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before your check-in date. If your reservation is non-refundable, you might be able to still cancel and receive a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Windham.
Where can I learn more about changing or cancelling my trip to Windham?
For more details about rescheduling or cancelling your trip to Windham, go to https://www.expedia.com/service/.
What's the best accommodation for families in Windham?
Wylder Hotel Windham is a hotel with an outdoor pool and a restaurant, and it's a top choice on Expedia for families. Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge is another good choice for your kid-friendly vacation. Attractions in the area like Zoom Flume and Pine Hill Community Center are also fun for kids of all ages. Find more child-friendly accommodations in Windham.
What's the best pet-friendly hotel in Windham?
Hotel Vienna is a top dog-friendly hotel, and offers an indoor pool along with free WiFi for its human guests. Two other good options for you and your pet's trip include Eastwind Windham and Wylder Hotel Windham. See more pet-friendly hotel accommodations in Windham.
What's the best place to stay close to Windham Mountain Resort?
Winwood Inn & Condominiums is one of the top choices for your stay based on our traveler data, and this 3-star resort offers a restaurant and free parking. It's located 1.5 mi (2.5 km) from Windham Mountain Resort.
What about the best place to stay close to Windham Vineyards and Winery?
One of the top choices for your stay is Cave Mountain Motel, located 2.4 mi (3.8 km) from Windham Vineyards and Winery, and this property offers free breakfast and free parking.
What's the best golf hotel in Windham?
Hotel Vienna is a top hotel that has an adjacent golf course and features free breakfast. Another good choice is Albergo Allegria Hotel & Breakfast Restaurant if you'd like to stay near a golf course while in town. You can tee off at Windham Country Club during your trip. See more golf hotels in Windham.
What's the best place to stay to stay near the slopes in Windham?
Winwood Condominiums by Windham Mountain Club is a top hotel for a winter getaway, and features a free ski shuttle and free WiFi. This hotel is adjacent to Windham Mountain Resort. Other good options for your winter getaway include Antique Rose Inn Windham and The Outpost by Windham Mountain Club. See all ski hotels in Windham.
What are some accommodations with pools in Windham?
Hotel Vienna: Hotel located near Windham Mountain Resort. Features daily, an indoor pool, and free self parking. Wylder Hotel Windham and Winwood Condominiums by Windham Mountain Club are two additional hotels that feature an onsite pool. View all hotels with pools in Windham.
What is the best spa hotel in Windham?
Mountainside by Windham Mountain Club is a highly recommended spa hotel with an outdoor pool. Spend an afternoon at The Spa where you'll find Swedish massages, deep-tissue massages, and hot stone massages and more. See all spa hotels in Windham.
What's the best hotel in Windham with a water park on-site or close by?
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge is a popular lodge featuring in-room kitchens and water park access. You'll find Zoom Flume within 18 minutes by car. Check out all hotels with or near waterparks in Windham.
What's the best hotel for staying near Albany International Airport (ALB)?
Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.
What is staying in Windham like?
Visitors to Windham are sure to enjoy the ski areas, mountain views, and coffeehouses. Tourists can also enjoy the city's breweries, golf courses, and wineries. A top sight in the area is Hunter Mountain. In Windham, there are 278 hotels and other accommodations to choose from. Find out more about Windham.
What should I do while I'm visiting Windham?
Skiing is a great activity, and Windham Country Club is one place to visit. Additionally, you'll find Hunter Mountain in the area. Check out what more to see and do in Expedia's Windham guide.
What's the weather like in Windham?
The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Windham are January, March, December, and November, with each month seeing an average of 7 inches of snowfall.

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