Windham Hotels from S$109

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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, (736)
Unwind at this mountain retreat featuring an indoor pool and complimentary breakfast. Borrow free bikes to explore nearby trails or take a 5-minute drive to hit the slopes at Windham Mountain Resort. Guests rave about the helpful staff and prime location.

"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, (91)
Splash in the outdoor pool at this mountain getaway, just 5 minutes from Windham Mountain Resort. Enjoy refreshments at the coffee shop or bar after a day of adventure. Free WiFi and parking add convenience to your stay.

"Very nice hotel. Exactly what we needed."
United States
Nicolas
The price is S$339
includes taxes & fees
9 Jan - 10 Jan
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 S$261
includes taxes & fees
8 Jan - 9 Jan
Winwood Condominiums by Windham Mountain Club

Antique Rose Inn Windham

Antique Rose Inn Windham
3.0 star property
Windham
9.0 out of 10, Wonderful, (125)
Ski enthusiasts will love this charming bed & breakfast, offering free perks like a daily full breakfast, WiFi, and parking. The Victorian property includes a terrace and garden, with ski passes available. Located near Windham Country Club.

"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 S$187
includes taxes & fees
8 Jan - 9 Jan
Antique Rose Inn Windham

Eastwind Windham

Eastwind Windham
2.0 star property
Windham
9.2 out of 10, Wonderful, (80)
Surrounded by scenic beauty, this hotel offers easy access to Windham Mountain Resort and Country Club. Enjoy relaxation with free WiFi and parking while unwinding with a drink at the welcoming bar after an adventurous day.

"I loved our stay!"
United States
Erika
The price is S$911
includes taxes & fees
16 Jan - 17 Jan
Eastwind Windham

The Outpost by Windham Mountain Club

The Outpost by Windham Mountain Club
2.5 star property
Windham
8.6 out of 10, Excellent, (4)
Stay steps from Windham Mountain Resort with this hotel's free ski shuttle and WiFi. After hitting the slopes, unwind in the outdoor pool. Windham Country Club is nearby, and free parking adds convenience to your mountain getaway.

"Cozy and warm. I think it would be better to visit during the winter season"
United States
TAEJUN
The price is S$623
includes taxes & fees
9 Jan - 10 Jan
The Outpost by Windham Mountain Club

Albergo Allegria Hotel & Breakfast Restaurant

Albergo Allegria Hotel & Breakfast Restaurant
3.5 star property
Windham
9.6 out of 10, Exceptional, (270)
Surrounded by outdoor adventure, this charming B&B offers free WiFi and parking just 5 minutes from skiing. Hiking trails, kayaking, and mountain biking await, while the garden, terrace, and bike cleaning station welcome you back after exploring.

"Nice people and great breakfast. "
United States
Remelin
The price is S$185
includes taxes & fees
8 Jan - 9 Jan
Albergo Allegria Hotel & Breakfast Restaurant

Beds on Clouds

Beds on Clouds
3.0 star property
Windham
7.4 out of 10, Good, (68)
Tranquil retreat near Windham Mountain Resort and Country Club. Enjoy rejuvenating massages and manicures after a day outdoors. Free WiFi and parking enhance your stay, with garden and terrace spaces for relaxation.

"Great spot for a weekend getaway"
United States
Bertrand
The price is S$261
includes taxes & fees
8 Jan - 9 Jan
Beds on Clouds

The Haüs Windham

The Haüs Windham
2.0 star property
Windham
8.2 out of 10, Very good, (21)
Experience the charm of this mountain retreat just minutes from Windham Mountain Resort. Enjoy complimentary WiFi and parking while exploring nearby skiing and snowboarding trails. Windham Country Club awaits after a day of alpine adventure.

"Great place nice and clean"
United States
henry
The price is S$322
includes taxes & fees
13 Jan - 14 Jan
The Haüs Windham

Cave Mountain Motel

Cave Mountain Motel
2.5 star property
Windham
9.4 out of 10, Exceptional, (135)
Embrace alpine charm at this motel with complimentary buffet breakfast, WiFi, and parking. Just 5 minutes from Windham Mountain Resort, it offers easy access to hiking trails, vineyards, and winery attractions.

"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 S$192
includes taxes & fees
8 Jan - 9 Jan
Cave Mountain Motel

The Perch Hotel

The Perch Hotel
2.0 star property
Cornwallville
9.4 out of 10, Exceptional, (23)
Set in Cornwallville, this hotel provides easy access to Windham Mountain Resort, just a 15-minute drive away. Guests enjoy premium bedding, free WiFi, and complimentary parking, with Zoom Flume and Durham Centre Museum nearby.

"This place is great!! Awesome view with a pool table and fireplace in the common area. Very home feeling with the decor, place was clean and tidy."
United States
Michael
The price is S$497
includes taxes & fees
9 Jan - 10 Jan
The Perch Hotel

Twin Gables of Woodstock

Twin Gables of Woodstock
3.0 star property
Woodstock
9.8 out of 10, Exceptional, (193)
This charming hotel offers complimentary breakfast, WiFi, and parking. Outdoor enthusiasts can enjoy nearby hiking trails, kayaking, and mountain biking. The Victorian property features a garden and terrace, and sits close to Woodstock Public Library.

"Amazing stay!!! Super hippie vibe and lived every minute of it. "
United States
Heather
The price is S$185
includes taxes & fees
8 Jan - 9 Jan
Twin Gables of Woodstock

The Herwood Inn

The Herwood Inn
4.5 star property
Woodstock
9.8 out of 10, Exceptional, (94)
This charming guesthouse offers a hot tub and complimentary bicycles, perfect for exploring nearby hiking trails. Close to The Comeau Property and Woodstock Public Library, guests enjoy free WiFi, parking, and a peaceful garden terrace in this beautiful mountain setting.

"Great property, room, location & staff."
United States
Joseph
The price is S$187
includes taxes & fees
12 Jan - 13 Jan
The Herwood Inn

Woodstock Way Hotel

Woodstock Way Hotel
4.0 star property
Woodstock
9.6 out of 10, Exceptional, (220)
Nestled near the train station in artistic Woodstock, this tranquil hotel offers deep-tissue massages and on-site spa services. Unwind at the bar or café after exploring nearby SweetHeart Gallery, all with free WiFi and parking.

"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, (156)
Set amid Woodstock's artistic community, this charming B&B offers free breakfast and parking. Guests can enjoy outdoor tennis courts or explore nearby attractions like The Comeau Property, with kayaking and mountain biking options for adventure seekers.

"Diane was a very gracious host of her lovely BnB! My privacy was well respected and check in/out was easy as pie! Thank you!"
United States
Andrew
The price is S$271
includes taxes & fees
8 Jan - 9 Jan
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)
Charming hotel along the millstream offers tranquil gardens and a welcoming terrace. Just minutes from the Woodstock Artists Association, guests enjoy complimentary WiFi and continental breakfast while exploring local galleries.

"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 S$257
includes taxes & fees
11 Jan - 12 Jan
The Woodstock Inn on the Millstream

Black Bear Lodge

Black Bear Lodge
2.5 star property
Prattsville
9.0 out of 10, Wonderful, (131)
Peaceful lodging surrounded by nature, where complimentary parking and WiFi enhance your stay. Close to Ashland Park and Bearpen Mountain State Forest, this tranquil motel offers daily housekeeping for a refreshing mountain getaway.

"A great place to stay in the Catskills at a reasonable price point. "
United States
Peter
The price is S$206
includes taxes & fees
8 Jan - 9 Jan
Black Bear Lodge

The Colonial Motel

The Colonial Motel
2.5 star property
Grand Gorge
9.4 out of 10, Exceptional, (409)
Set near hiking trails, kayaking spots, and cross-country skiing areas, this clean motel provides refreshing comfort with a seasonal outdoor pool. The helpful staff ensures a pleasant stay while nearby Gilboa and Pratt museums offer cultural exploration.

"Very friendly staff. Room is clean."
United States
Yan
The price is S$126
includes taxes & fees
8 Jan - 9 Jan
The Colonial Motel

Moore's Motel

Moore's Motel
2.5 star property
Prattsville
8.6 out of 10, Excellent, (159)
Tranquil accommodation provide a restful atmosphere at this Prattsville motel. Take a refreshing dip in the outdoor pool after exploring nearby Pratt Museum. Free WiFi and parking add value to this peaceful getaway.

"No frills, great value, friendly owners, clean rooms, hot showers with great pressure, heat worked well. Will return. "
United States
John
The price is S$166
includes taxes & fees
8 Jan - 9 Jan
Moore's Motel

Catskill Seasons Inn

Catskill Seasons Inn
2.5 star property
Shandaken
8.2 out of 10, Very good, (246)
Tucked away in the Catskills, this charming inn offers a seasonal outdoor pool and tennis courts. Just minutes from Belleayre Mountain Ski Centre with free breakfast, WiFi and parking for a relaxing mountain retreat.

"Great stay!!! "
United States
Jordana
The price is S$211
includes taxes & fees
12 Jan - 13 Jan
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.
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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

Find out more about Windham

Top reasons to visit Windham

  • Thrilling Skiing: Windham Mountain offers excellent skiing opportunities, making it a perfect destination for winter sports enthusiasts.
  • Scenic Nature Walks: Enjoy beautiful hiking trails and explore nearby waterfalls and national parks during warmer months.
  • Charming Accommodations: A variety of lodgings, from pet-friendly hotels to unique agritourism properties, cater to all visitors.
  • Vineyard Tours: Experience local vineyards, providing a delightful taste of the region’s wines and scenic landscapes.
  • Family-Friendly Atmosphere: Windham's welcoming communities and outdoor activities make it ideal for families and couples alike.

Find great hotels in and around Windham

Discover the charming hotel options in Windham, New York, ideal for adventurous travellers and families alike. From pet-friendly accommodations to agritourism properties, there's a variety to suit your needs. Whether you're seeking the comfort of Wyndham hotels or the unique experience offered by the Wylder Hotel Windham, you'll find a welcoming atmosphere that caters to all types of visitors looking for a memorable stay in this picturesque destination.

  • Hunter Lodge, a Bluebird by Lark: Nestled 12.9km from Windham, Hunter Lodge offers a vibrant getaway for adventurers and LGBTQIA travellers alike. This welcoming accommodation provides a range of adventure sports both onsite and nearby, including canoeing, kayaking, snowboarding, and mountain biking. With a pet-friendly policy, it caters to furry companions, allowing dogs with provisions like food and water bowls. Designed for those seeking thrill and inclusivity, Hunter Lodge is a unique destination for an adventurous holiday.
  • Hotel Vienna: Located in the heart of Windham, Hotel Vienna harmonises business efficiency with adventure. Ideal for business travellers and pet owners, it provides essential facilities for work while also offering recreational activities like skiing, zip-lining, and hiking in the surrounding areas. Pets are welcome, with amenities designed to ensure their comfort. The hotel’s blend of convenience and adventure makes it an excellent choice for those looking to mix business with pleasure.
  • Hotel Mountain Brook: Situated 16.1km from Windham, Hotel Mountain Brook is a charming 4-star retreat perfect for adventure enthusiasts and pet lovers. Guests can explore a variety of outdoor activities, including hiking, fishing, and birdwatching, all within easy reach. The hotel allows pets, ensuring a homely atmosphere for furry friends. With its commitment to adventure and comfort, Hotel Mountain Brook promises a memorable stay in a picturesque setting.

Where to stay in and around Windham

Windham, New York, offers an idyllic escape for those seeking adventure and relaxation alike. Embrace thrilling skiing opportunities in winter, while the stunning scenery invites hiking and exploration in warmer months. Nearby, charming communities enhance the experience with a friendly, family-oriented atmosphere. Perfect for city getaways or romantic weddings, Windham's breathtaking landscapes and tranquil vibes provide an unforgettable vacation destination for all types of travellers.

  • Hunter: Nestled around 11.3km from Windham, Hunter is a vibrant city that attracts visitors year-round, especially during the winter months from December to February when skiing enthusiasts flock to its renowned slopes. The region offers a plethora of adventure and sports experiences, boasting ski resorts and expansive ski fields. In addition to winter activities, Hunter is surrounded by stunning natural landmarks, including mountains, serene lakes, and picturesque waterfalls, making it a great destination for those who love the outdoors.
  • Hensonville: Located a mere 3.2km from Windham, Hensonville is a charming city that experiences peak visitor numbers during the summer months of June to August. Like Hunter, it is a hotspot for skiing and outdoor adventures, with excellent access to ski resorts and fields. Beyond winter sports, visitors are drawn to Hensonville’s natural beauty, where mountains, lakes, and waterfalls create a tranquil backdrop for exploring the great outdoors. Whether you're skiing down the slopes or enjoying a peaceful hike, Hensonville offers a delightful experience for all.
  • East Windham: Situated in close proximity to Windham, East Windham is a quaint village that invites adventurers to explore its captivating landscapes. With peak visitation in the summer and autumn months, this village is perfect for those seeking outdoor activities ranging from skiing to hiking in the nearby national state park. East Windham also features a theme park, enhancing its appeal for families and thrill-seekers alike. With its charming atmosphere and abundant recreational opportunities, East Windham is a fantastic addition to your itinerary.

Things to do in and around Windham

Windham, New York, is an ideal destination for ski enthusiasts and adventure seekers alike. Visitors can enjoy a range of activities, including skiing at the renowned ski resort, embarking on exhilarating motorhome adventures, and exploring local vineyard tours. With a plethora of fun activities available, Windham promises an unforgettable experience for those looking to immerse themselves in the great outdoors.

Shopping

In Windham, you can visit the Woodstock Music Shop, 32.2km away, for unique gifts. Vinnie's Farm Market, located 27.4km away, offers local produce and crafts. If you're up for a drive, the Hudson Valley Mall, 43.5km away, features a variety of shops and entertainment options.

Recreation

At Windham Country Club, enjoy a round of golf surrounded by scenic landscapes and invigorating outdoor vibes. Just 17.7km away, Blackhead Mountain Country Club offers a similar experience for golf enthusiasts. For ultimate relaxation, visit Copperhood Retreat & Spa, 24.1km from Windham, where wellness and rejuvenation await.

Adventure

Windham Mountain Resort is an exhilarating ski resort offering fantastic slopes for skiing and snowboarding amidst stunning winter scenery. For a splash of fun, visit Zoom Flume, a family-friendly waterpark with thrilling slides and water attractions. For ski enthusiasts, the Zephyr Express Ski Lift provides easy access to pristine slopes.

Nightlife

Experience the vibrant nightlife in Windham with a visit to Mount Tremper Arts, only 29.0km away, offering a cultural atmosphere. Alternatively, enjoy the Colony Theatre, 32.2km distant, or the Ulster Performing Arts Center, 46.7km away, both promising engaging performances and a warm, family-friendly vibe.

*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 during your visit to Windham, consider travelling in the off-peak months of March to April and November, when accommodation prices are lower. Tuesdays are the best days for budget stays, while Fridays tend to be the most expensive. Use Expedia’s search tools to filter by budget and hotel type, and take advantage of package deals that combine flights and activities for extra savings. Additionally, explore free outdoor activities and utilise public transport for an economical way to get around the area.

  • 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: Expedia’s search tool enables you to specify your budget, preferred location, and additional preferences. You can sort your results from the lowest to the highest prices, allowing you to view the most affordable hotels first. Additionally, you have the option to refine your search by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels that are available for booking.
  • Consider bundling your trip: You can save money by combining your Windham hotel reservation with your flights and activities through an Expedia package.

Find the best attractions in and around Windham

Windham, New York, is a fantastic destination for adventure and sports enthusiasts, offering a range of activities from skiing at Windham Mountain to exploring nearby waterfalls and national state parks. Visitors can immerse themselves in the outdoors, culture, and thrilling experiences, making it ideal for those seeking an active holiday. Whether you're hitting the slopes or enjoying scenic nature walks, Windham has something for every adventurous traveller.

  • Windham Mountain Resort: Experience the thrill of skiing at Windham Mountain Resort, where adventure meets breathtaking outdoor scenery. Whether you're a novice or an expert, the diverse slopes cater to all skill levels, surrounded by stunning mountain vistas.
  • Catskill State Park: Discover the natural beauty of Catskill State Park, located 22.5km from Windham. This expansive park offers a plethora of outdoor activities, including hiking, birdwatching, and picnicking, amidst serene landscapes and lush forests.
  • Kaaterskill Falls: Visit Kaaterskill Falls, a stunning 19.3km trek from Windham, where romance and adventure intertwine. Marvel at the cascading waters and enjoy picturesque hiking trails that provide a perfect backdrop for memorable moments.

Best time to go to Windham

The best time to visit Windham is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. January is its coolest month on average. At this time, 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

Accessing Windham, New York, is convenient via several major airports. Newburgh, NY (SWF-Stewart Intl.) is 90.1km away, with nearby hotels like The Dutchess Inn and Spa at Beacon, 9.7km from the airport, and The Crossroads Hotel, just 3.2km away. Hudson, NY (HCC-Columbia County) is 45.1km from Windham, featuring the 4-star Wick, Hudson, 8.0km from the airport. Lastly, Albany, NY (ALB-Albany Intl.) is 61.2km away, with options like Crowne Plaza Albany, only 1.6km from the airport. Each airport offers transport services to local hotels, ensuring easy access for your stay.

Frequently asked questions

What's the best place to stay in Windham?
Hotel Vienna is a favourite with Expedia customers. This hotel offers free breakfast and an indoor pool. Reviews from our site also recommend Eastwind Windham and Wylder Hotel Windham as top choices for your stay. See all available top hotels, or vacation rentals in Windham.
If I need to cancel my hotel reservation in Windham, will I receive a refund?
Yes! Most hotel bookings are refundable if you cancel prior to the hotel's cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If you have a non-refundable reservation, you might still have the option to cancel and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Windham.
What's the best family accommodation 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. Also, attractions in the area such as Zoom Flume and Pine Hill Community Center are fun for children of all ages. Find more child-friendly accommodations in Windham.
What's the best dog-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 to stay with your pet include Eastwind Windham and Wylder Hotel Windham. See more pet-friendly hotel accommodations in Windham.
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 hotel for a trip to 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 WiFiThis hotel is adjacent to Windham Mountain Resort. Other good options for your ski trip include Antique Rose Inn Windham and The Outpost by Windham Mountain Club.
What are some accommodation options 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 offer an on-site 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 is staying in Windham like?
Visitors to Windham will definitely enjoy the skiing, mountain views and cafes. 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 276 hotels and other accommodation options to choose from. Find out more about Windham.
What should I see while I'm in Windham?
Skiing is a great activity, and Windham Country Club is one place to visit. Additionally, you'll find Hunter Mountain in the area. Take a look at what more there is 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 temperature of 18°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Windham are January, March, December and November, with each month seeing an average of 18 cm of snowfall.

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