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Top Windham hotels

Albergo Allegria Hotel & Breakfast Restaurant

Albergo Allegria Hotel & Breakfast Restaurant

3.5 out of 5
43 State Route 296, Windham, NY
$145 nightly
The price is $157 total per night from Jul 22 to Jul 23
$157 total
Jul 22 - Jul 23
Total includes taxes and fees
A restaurant, free self parking, and a terrace are among this bed & breakfast's amenities. WiFi in public areas is free. A business center, a garden, and a lobby ...
Wonderful stay!
"We enjoyed our stay, the room was very comfortable, the bathroom very clean and convenient to town."

Reviewed on Jul 7, 2025

Albergo Allegria Hotel & Breakfast Restaurant
Hotel Vienna

Hotel Vienna

2.5 out of 5
107 State Route 296, Windham, NY
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $128 total per night from Aug 3 to Aug 4
$128 total
Aug 3 - Aug 4
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of ...
"Lovely accommodations and setting."

Reviewed on Jul 18, 2025

Hotel Vienna
Eastwind Windham

Eastwind Windham

2 out of 5
5088 NY-23, Windham, NY
$227 nightly
The price is $245 total per night from Jul 22 to Jul 23
$245 total
Jul 22 - Jul 23
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A bar/lounge is also provided.
"Friendly staff, accommodating and clean Some of it under construction"

Reviewed on May 23, 2025

Eastwind Windham
Cave Mountain Motel

Cave Mountain Motel

2.5 out of 5
10978 STATE RTE 23, Windham, NY
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $150 total per night from Jul 22 to Jul 23
$150 total
Jul 22 - Jul 23
Total includes taxes and fees
This motel features free WiFi in public areas, barbecue grills, and free self parking. Free buffet breakfast is served. A garden and a picnic area are also ...
"It was clean, convenient, and everything worked. Perfect!"

Reviewed on Jun 17, 2025

Cave Mountain Motel
Antique Rose Inn Windham

Antique Rose Inn Windham

3 out of 5
326 State Route 296, Windham, NY
$135 nightly
The price is $146 total per night from Jul 22 to Jul 23
$146 total
Jul 22 - Jul 23
Total includes taxes and fees
This bed & breakfast doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Enjoy the ski shuttle and onsite ski passes. ...
"We did not expect to share a bathroom. We should of done our homework on the place. Its a lovely place to stay. Owner is very friendly, breakfast was accommodating to our wishes."

Reviewed on Jun 29, 2025

Antique Rose Inn Windham
Winwood Condominiums by Windham Mountain Club

Winwood Condominiums by Windham Mountain Club

3 out of 5
5220 NY-23, Windham, NY
$178 nightly
The price is $192 total per night from Jul 22 to Jul 23
$192 total
Jul 22 - Jul 23
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi, free self parking, and a free ski shuttle. Take advantage of ski passes on site, and enjoy sledding. ...
Go for the views and town, stay for the pool
"Interesting place. Obviously a ski condo, so not too busy in the summer. Top-notch pool in a gorgeous setting. Rest of the complex was surprisingly ramshackle and of motel-like construction, unusual for a condo."

Reviewed on Jul 7, 2025

Winwood Condominiums by Windham Mountain Club
The Haüs Windham

The Haüs Windham

2 out of 5
218 NY-296, Windham, NY
$175 nightly
The price is $190 total per night from Jul 23 to Jul 24
$190 total
Jul 23 - Jul 24
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.
"Great place nice and clean"

Reviewed on Jul 20, 2025

The Haüs Windham
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
19 New York 296, Windham, NY
$216 nightly
The price is $234 total per night from Aug 18 to Aug 19
$234 total
Aug 18 - Aug 19
Total includes taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee ...
"The staff is absolutely incredible and the property has everything you need. We were taken care of the entire time we were there. The grounds are lovely. We would definitely stay here again."

Reviewed on Jul 14, 2025

Wylder Hotel Windham
A'Neils Windham Ski Lodge & Family Retreat

A'Neils Windham Ski Lodge & Family Retreat

Windham
This smoke-free vacation home's ski-in/ski-out access and water park are among the highlights. There's fun for all ages with a playground and an arcade/game ...
Perfect for a ski family gathering
"A wonderful space for a family reunion ski get away. Enough personal space for each while also offering great shared space for warm gatherings and meals. Host was very accommodating and easily available. We would definitely stay again!"

Reviewed on Dec 31, 2024

A'Neils Windham Ski Lodge & Family Retreat
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Windham Hotel & Travel Guide

Are you planning on traveling in Kingston and looking to book hotels somewhere in or around the Windham area? With 7 hotels on Travelocity within a 6-mile (10-kilometer) radius of the city center, it will be easy to find something appropriate.

The Beds on Clouds is the closest Travelocity hotel to central Windham and it is located just a brief drive away.

The Scribner's Catskill Lodge is 10 miles (15 kilometers) from the center of Windham. If you would prefer another option, the VanWinkle Inn is positioned 15 miles (25 kilometers) away. The Villa Vosilla Boutique Resort and also the Gavin's Irish Country Inn are some alternative places to stay in Windham.

Hoping to journey a little bit further afield? Hudson Valley has many beautiful things worth checking out. Hudson Valley offers rivers, valleys and rolling hills. Popular visitor sights are historic bridges and open-air markets. Outdoor-loving visitors might engage in rock climbing, hiking and sea kayaking in the region.

Saugerties is 20 miles (36 kilometers) to the southeast of Windham and features Opus 40 and Seamon Park. Saugerties hotels and apartments include the Howard Johnson Inn - Saugerties and Comfort Inn Saugerties. 19 miles (31 kilometers) east of Windham, you'll find Catskill, which features the Wolff's Maple Breeze Resort and The Kaaterskill. Should you choose to stay in Catskill, a couple of places to add to your itinerary are the Thomas Cole National Historic Site and Bailiwick Ranch and Discovery Zoo.

Before leaving town, don't miss out on cheering wildly with other spectators at a local match. Times Union Center is located 35 miles (56 kilometers) to the northeast of Windham. Find a Travelocity-listed room not far from the action at the Hilton Albany or the TownePlace Suites by Marriott Albany Downtown/Medical Center.

Albany International Airport is a primary entry point for flying in and out of Windham. You can find it 35 miles (60 kilometers) from the city center. For modern travelers who would find it convenient to find Travelocity-listed accommodation nearby, check out Albany Marriott or Homewood Suites by Hilton Albany.

Top reasons for your vacation to Windham

  • Outdoor Adventures: Windham, New York offers a range of outdoor activities, including skiing, hiking, and winter sports. With its close proximity to Windham Mountain and the Adirondack Mountains, adventure enthusiasts will have plenty of opportunities to explore and enjoy breathtaking views.
  • Friendly Family Atmosphere: Windham is known for its family-friendly atmosphere, making it an ideal vacation destination. Families can enjoy quality time together while engaging in various activities suitable for all ages.
  • Scenic Beauty: Windham is surrounded by natural beauty, with picturesque landscapes and stunning views of the mountains. Nature lovers will appreciate the opportunity to immerse themselves in the tranquil and scenic environment.
  • Cozy Coffeehouses: Windham boasts a selection of charming coffeehouses, perfect for relaxing and unwinding after a day of outdoor adventures. Enjoy a warm cup of coffee or hot chocolate while taking in the cozy atmosphere.
  • Memorable Family Vacation: Windham offers the perfect combination of outdoor fun and relaxation, making it an ideal destination for a memorable family vacation. Create lasting memories while enjoying the beauty and activities that Windham has to offer.

Find your favorite hotels in Windham

If you're planning a ski vacation in Windham, New York, you'll find a range of hotel accommodations to choose from. Whether you're looking for a cozy lodge with rustic charm or a luxurious resort with all the amenities, Windham has options to suit every taste and budget. Many hotels in the area offer convenient access to the slopes, as well as other outdoor activities such as hiking and snowshoeing. With its picturesque scenery and welcoming atmosphere, Windham is a great destination for a memorable winter getaway.

Hotel nameTypeStarsDescription
Hotel ViennaHotel2.5This 2.5-star rated hotel is a great option for your ski vacation. It is located close to various winter activities such as snowtubing, ziplining, snowshoeing, snowmobileriding, snowboarding, and crosscountryskiing. The hotel also offers a hot tub and kayaking facilities. With its proximity to the ski area and accessible amenities, Hotel Vienna is an excellent choice for a fun-filled ski vacation.
Winwood Inn & CondominiumsHotel3.0If you're looking for a 3.0-star rated hotel, Winwood Inn & Condominiums is a great option. It is conveniently located near the mountain and offers close proximity to activities like snowtubing, ziplining, basketball, snowshoeing, snowmobileriding, sledding, snowboarding, and crosscountryskiing. The hotel also provides comfortable accommodations and easy access to kayaking facilities.
Albergo Allegria Hotel & Breakfast RestaurantBed & breakfast3.5For a 3.5-star rated bed & breakfast experience, Albergo Allegria Hotel & Breakfast Restaurant is an ideal choice. It is located near snowtubing, ziplining, snowshoeing, snowmobileriding, caveexploring, fishing, sledding, snowboarding, and crosscountryskiing. The hotel also offers a picturesque view of the river and is a great option for those seeking a cozy and charming ski vacation.

Explore the best activities and sights in Windham

Looking to plan a ski vacation in Windham, New York? You're in for a treat! Windham offers a range of activities suitable for families, including skiing, hiking, and outdoor adventures. With its close proximity to Windham Mountain and the Adirondack Mountains, you'll have plenty of opportunities for winter sports and breathtaking views. Windham also boasts a selection of coffeehouses, perfect for cozying up after a day on the slopes. So pack your bags and get ready for a memorable family vacation filled with outdoor fun and relaxation in beautiful Windham!

  1. Windham Mountain Resort: Nestled among the mountains, Windham Mountain Resort offers a thrilling ski experience with its perfectly groomed slopes and breathtaking views. Feel the rush as you glide down the powdery snow, surrounded by a stunning natural landscape. After an exhilarating day on the slopes, unwind at the cozy mountain lodge and sip on a hot cup of coffee, taking in the serene atmosphere. For outdoor enthusiasts, there are endless opportunities for hiking, hunting, and canoeing, allowing you to explore the beauty of nature. And if you're a fan of golf, tee off at the picturesque golf course, enjoying a game amidst the scenic mountains. Windham Mountain Resort is the perfect destination for adventure seekers and nature lovers alike.
  2. Windham Country Club: Set against a backdrop of majestic mountains, Windham Country Club offers an unforgettable golfing experience. Tee off amidst the lush green fairways, surrounded by the beauty of nature. As you play, soak in the tranquil atmosphere and enjoy the panoramic views of the mountains. After a round of golf, relax at the clubhouse, sipping on a refreshing coffee and relishing the peaceful surroundings. For those seeking adventure, explore the hiking trails or indulge in some hunting amidst the picturesque landscape. And if you're a fan of water activities, take a leisurely canoe ride on the serene waters. Windham Country Club is the ultimate destination for sports enthusiasts and those looking to reconnect with nature.
  3. Windham Vineyards and Winery: Immerse yourself in the romance and beauty of Windham Vineyards and Winery. Surrounded by rolling mountains, this winery offers a unique experience for wine lovers. Savor the exquisite flavors of their handcrafted wines, made from carefully selected grapes grown in the scenic vineyards. Relax on the patio with a glass of wine, taking in the breathtaking views of the mountains. For a bit of adventure, go hiking through the vineyards or embark on a kayaking journey on the nearby river. And if you're seeking tranquility, find a secluded spot to enjoy a cup of coffee amidst the peaceful surroundings. Windham Vineyards and Winery is the perfect destination for outdoor enthusiasts, wine connoisseurs, and those looking for a romantic experience.

Best times to go to Windham

The travel seasons of Windham

Trips to Windham show no change in popularity throughout the year. The peak season to visit is from December to February, with January being the highest month. Off-peak season starts from April to June, and October sees the least travelers.

Windham has something in store for you whenever you visit. January is the coldest month of the year, while July is hottest, with average temperatures up to 68.7 degrees Fahrenheit. The wettest month in Windham is July, so pack accordingly.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationcloud iconCloudiness
January22.1°F (-5.5°C)Light RainMostly Cloudy
February24.1°F (-4.4°C)Light RainMostly Cloudy
March31.6°F (-0.2°C)Light RainMostly Cloudy
April43.3°F (6.3°C)Light RainMostly Cloudy
May55.6°F (13.1°C)Light RainMostly Sunny
June63.0°F (17.2°C)Light RainMostly Sunny
July68.7°F (20.4°C)Light RainMostly Sunny
August66.7°F (19.3°C)Light RainMostly Sunny
September59.9°F (15.5°C)Light RainMostly Sunny
October48.9°F (9.4°C)Light RainMostly Sunny
November36.7°F (2.6°C)Light RainMostly Sunny
December28.8°F (-1.8°C)Light RainMostly Cloudy

Food and dining in Windham

When visiting Windham, New York, you'll be delighted by the local cuisine options. The Millrock is a popular restaurant known for its delicious North American dishes. If you're looking for a bistro experience, Bistro Brie & Bordeaux is highly rated and offers a variety of delectable options. Neapolis Pizzeria & Grille is a great choice for those craving pizza and other grilled specialties. Don't forget to visit Park Place for a delightful brunch experience and the B&B Lounge of Catskill for a cozy atmosphere. The postcard-esque surroundings of Windham add to the charm as you enjoy the culinary delights of the Upper Whistler region.

How do I find a great hotel with Travelocity?

Give your entire crew a vacation they'll never forget. When looking for the ideal accommodations, utilize the family-friendly badge to find hotels that offer additional amenities for children. Furthermore, our personalized filters assist you in finding hotels that are in close proximity to popular attractions, provide enhanced cleaning, and fit within your budget.

Why should I book with Travelocity?

Conference calls, to-do lists, and, of course, football practice. Busy lives and packed schedules call for trips that are hassle-free. Our aim is to provide stress-free travel every time you and your family book with us so that you can spend less time worrying and more time creating lasting memories. To achieve this, we will assist you in finding and planning your ideal trip, as well as offering transparent pricing and trustworthy reviews. We are committed to providing 24/7 guaranteed customer support before, during, and after your vacation.

How can I save money on my trip to Windham?

To save money on your trip to Windham, New York, consider visiting during the less popular season from April to June. This will not only save you money but also allow you to avoid the crowds. Additionally, bundle your flights, hotel, and car bookings together to take advantage of discounted prices. While in Windham, take advantage of the inexpensive local affinities such as hiking in the beautiful mountains, exploring the nature trails, and enjoying a relaxing day at a nearby winery. These activities will provide memorable experiences without breaking the bank.

Frequently asked questions

What are the top kid-friendly hotels in Windham?
Take some of the hassles out of traveling with youngsters by opting for a family-friendly Windham hotel. From thoughtful amenities to services that bring a smile, these properties come with perks that'll help make your getaway plain sailing: Your entourage will love staying at Restored Firehouse One Minute to Skiing on Main St. A water park and animal viewing activities are just a couple of the things that help make this property an attractive option. Alternatively, spend your Windham getaway at TOWNHOUSE-LOFT-30 ft balcony Mt View/6 BEDS/ Sleeps 6. Make the most of free WiFi, internet access and more here.
Where can I find cheap hotels in Windham?
At Travelocity you'll find really nice hotels in Windham at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Windham rather than in Windham. We may find you even better rates, too.
How do I find the best Windham hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Windham then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Windham?
The cheapest hotel in Windham is $128. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Windham?
There are 2,065 hotels in Windham on Travelocity.
What are the best hotels in Windham?
Windham has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Windham for you!
When is the best time to visit Windham?
If you want the joy of a fun-filled trip in peak season, visit Windham during November, December and January. If you'd prefer the peace of off-season, book a stay during quieter months, such as April, May and October.
When is the cheapest time to stay in Windham?
Based on historic data is usually the cheapest month to visit Windham. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Windham?
There are multiple hotels in Windham that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Windham. We have plenty of kid-friendly hotels in Windham to choose from on Travelocity!
Why book a hotel in Windham through Travelocity?
Because we have the top hotels in Windham! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Windham on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

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