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Find Hotels in Windham, NY

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Windham hotels and places to stay

Waterfront Secluded Log-house W/sauna, Games, More, Mins To Town & Activities
4.9/5Exceptional! (22 reviews)
Wonderful time!

"House is well kept and cozy! We really enjoyed our weekend. We didn’t ski but you can see the mountain from the house, would be a great ski house! Would definitely stay here again."…"

Reviewed on Mar 23, 2020

Waterfront Secluded Log-house W/sauna, Games, More, Mins To Town & Activities
The Cutest Cabin & NEW HOT Tub, Fire pit & BBQ Grill
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1.44 mi from city center
5/5Exceptional! (43 reviews)
Relaxing

"Relaxing. Wish it was a bit more seclusive"…"

Reviewed on Mar 25, 2020

The Cutest Cabin & NEW HOT Tub, Fire pit & BBQ Grill
Cozy Catskill Chalet w/ Hottub
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1.87 mi from city center
4.9/5Exceptional! (9 reviews)
Cozy chalet happiness

"The house was super cute and super quaint! Perfect for 4 to 5 guests And conveniently located right near Windham mountain. The house is perfect for an easy getaway. The ultimate peaceful non materialist getaway!"…"

Reviewed on Jan 27, 2020

Cozy Catskill Chalet w/ Hottub
Exclusive, Exquisite & Unforgettable MTN Oasis NOW Offered FOR Long Term Rent
5/5Exceptional! (1 review)
Wonderful Windham retreat

"Property was stunning! Spacious and beautifully designed- great location and great amenities too The property manager went above and beyond to help us all week helping us ... she was just fantastic ! New house so there were a few glitches but overall ... Amazing"…"

Reviewed on Jan 3, 2020

Exclusive, Exquisite & Unforgettable MTN Oasis NOW Offered FOR Long Term Rent
NEW! 5BR Windham Home w/Game Room, Hot Tub & Views!! AMAZING 360* of mountain 👌
5/5Exceptional! (4 reviews)
Great Family Home

"This is a great house for an extended family to gather and enjoy time together! The living room and dining area are large. We all loved the game room and especially enjoyed playing basketball and sitting in the hot tub. My 6 year old granddaughter counted 12 televisions! We discovered that the town ..."…"

Reviewed on Mar 8, 2020

NEW! 5BR Windham Home w/Game Room, Hot Tub & Views!! AMAZING 360* of mountain 👌
Antique Rose Inn Windham
3 out of 5
326 State Route 296, Windham, NY
The price is $110 per night
3.56 mi from city center
4.6/5Wonderful! (51 reviews)

"Loren is a doll, so welcoming and makes a delicious breakfast. The property is spotless and our room was extremely comfortable and homey. This is a lovely spot to stay in Windham!"…"

Reviewed on Feb 9, 2020

Antique Rose Inn Windham
Winwood Inn & Condominiums
3 out of 5
5220 NY-23, Windham, NY
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2.01 mi from city center
4.2/5Very Good! (166 reviews)

"Very clean and cozy. All the staffs were very friendly. Loved the restaurant w/bar downstairs. Firepit in front is special! Enjoyed a glass of wine after skiing. Only wishes would be having a refrigerator and more lights in the room especially in the vanity area. Overall, it was a nice stay with ..."…"

Reviewed on Feb 26, 2020

Winwood Inn & Condominiums
Beds on Clouds
3 out of 5
5320 Main Street, Windham, NY
The price is $119 per night
1.8 mi from city center
3.9/5Very Good! (42 reviews)

"The owners were extremely hospitable and accommodating. The breakfast was delicious."…"

Reviewed on Jan 1, 2020

Beds on Clouds
Albergo Allegria Hotel & Breakfast Restaurant
3.5 out of 5
43 State Route 296, Windham, NY
The price is $109 per night
2.62 mi from city center
4.8/5Exceptional! (134 reviews)

"It was so welcoming and so cute! It was also so close to windham mountain it was a perfect b&b to stay at"…"

Reviewed on Mar 2, 2020

Albergo Allegria Hotel & Breakfast Restaurant
The Thompson House
2.5 out of 5
19 Rt. 296, Windham, NY
The price is $115 per night
2.53 mi from city center
4/5Very Good! (40 reviews)
Peaceful stay

"Very enjoyable and accommodating hotel. Quaint and comfortable."…"

Reviewed on Dec 27, 2019

The Thompson House
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Visiting Windham

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.

  • You'll find 268 Expedia hotels and other accommodations in the larger area of Kingston
  • The closest major airport is in Hudson, NY (HCC-Columbia County), 28.9 mi (46.6 km) from the city center
  • The next closest is in Albany, NY (ALB-Albany Intl.), 37.5 mi (60.3 km) away

Sightseeing and Staying in Windham

Skiing is just one of the top activities, while Windham Mountain Resort and Windham Country Club are sights to visit. Additionally, you might want to add Windham Vineyards and Winery to your agenda.

As you plan your holiday retreat, you'll find 27 hotels and other lodging options to pick from in Windham. Below are top ranked ones based on our user reviews:

  • Albergo Allegria Bed and Breakfast Hotel - This 3.5-star bed & breakfast features free breakfast, free WiFi, and free parking. It's a favorite with Expedia travelers for its helpful staff and comfortable rooms.
  • Antique Rose Inn Windham - Our customers like the breakfast and room size at this B&B. With a stay at this 3-star bed & breakfast, guests can enjoy access to free breakfast and free parking, along with free WiFi.
  • Hotel Vienna - This 2.5-star hotel features free breakfast, an indoor pool, and free WiFi. Expedia customers like its breakfast and pool.

Dressing for Windham

  • Between January and March, daytime temperatures average 51°F, while nighttime temperatures stay around 14°F
  • From April to June, the average is 81°F during the day and 32°F at night
  • July through September sees average temperatures of 83°F during the day and 45°F at night
  • In October-December, you can expect 66°F as the daytime average and 16°F as the nighttime average
  • Windham gets about 39.41 inches of rain per year
  • July and August are usually the hottest months averaging 81°F, while January and February are usually the coldest with an average temperature of 16°F

Frequently asked questions

What's the best place to stay in Windham?
Catskill Lodge is a favorite with Expedia customers. This 3-star B&B offers free breakfast and free WiFi. Winwood Inn & Condominiums is another top choice for your trip based on traveler reviews.
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. Enter dates in and click on “Search”, then use the filter option “free cancellation” to get the best 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 place to stay on a budget in Windham?
Based on reviews, Copper Kettle Cottages is a popular 2.5-star property for our travelers looking for an economical choice, and features free WiFi and free parking.
What's the best accommodation for families in Windham?
Antique Rose Inn Windham is a top 3-star B&B on Expedia for families, and features free parking and free breakfast. Other good choices to stay with the kids include Winwood Inn & Condominiums and Albergo Allegria Hotel & Breakfast Restaurant. Attractions in the area like Zoom Flume and Bailiwick Ranch and Discovery Zoo are also fun for kids of all ages.
What's the best hotel for couples in Windham?
Albergo Allegria Hotel & Breakfast Restaurant is a favorite 3.5-star B&B for couples, and features premium bedding and free WiFi. Other good options for your romantic getaway include Hotel Vienna and Winwood Inn & Condominiums.
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 full-service spa and free breakfast. It’s located just a short 1 mi (1.6 km) from Windham Mountain Resort. Other good options close by include Beds on Clouds and ON Mountain - 4 Bed, 4 Bath Retreat - Walk TO Slopes!.
What about the best place to stay close to Windham Vineyards and Winery?
One of the top choices for your stay is Winwood Inn & Condominiums, located 3.7 mi (6 km) from Windham Vineyards and Winery, and this 3-star resort offers a full-service spa and free breakfast. Cave Mountain Motel and Beds on Clouds are a couple of other good options within a few miles.
What's the best golf hotel in Windham?
The Thompson House is a top hotel that has an adjacent golf course and features free WiFi. Other good options to stay near a golf course include Copper Kettle Cottages and Hotel Vienna. You can tee off at Windham Country Club during your trip.
What's the best place to stay to stay near the slopes in Windham?
Based on our travel data, Georgian Garden Inn is a top 3-star B&B for a winter vacation, and features ski storage and free WiFi. Other good choices for your winter getaway include Copper Kettle Cottages and Winwood Inn & Condominiums. Enjoy the skiing and snowboarding by visiting Windham Mountain Resort or Hunter Mountain.
What are some accommodations with pools in Windham?
The Thompson House is a top hotel with a pool, free WiFi, and free parking.
What is the best spa hotel in Windham?
Hotel Vienna is a top spa hotel with 30 rooms, free WiFi, and off-street parking. Why not spend some time relaxing in the spa tub? Another popular spa hotel in Windham is Winwood Inn & Condominiums.

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