Windham, NY

Travel Guide

A winding road through a forest with autumn foliage, a rocky cliff on the right, and a mountain in the background.
A canoe on a calm lake with a forested shoreline.
A river surrounded by autumn foliage.
A snowy ski slope with trees on either side and a view of the valley below.
Two skiers on a snowy slope with a valley and mountains in the background.
Hotel Vienna

Hotel Vienna

3 out of 5
107 State Route 296 Windham NY
$145 nightly
The price is $157 total per night from Oct 1 to Oct 2
$157 total
Oct 1 - Oct 2
Total with taxes and fees
Book a stay at this golf hotel in Windham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
9.4/10 Exceptional! (878 reviews)
"Very nice property with very nice rooms and great staff. Would definitely recommend!"

Reviewed on Sep 25, 2026

Hotel Vienna
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
19 New York 296 Windham NY
$361 nightly
The price is $390 total per night from Oct 29 to Oct 30
$390 total
Oct 29 - Oct 30
Total with taxes and fees
Stay at this hotel in Windham. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Windham Mountain Resort and Windham Country Club are located ...
Wylder Hotel Windham
Eastwind Windham

Eastwind Windham

3.5 out of 5
5088 NY-23 Windham NY
$319 nightly
The price is $344 total per night from Oct 1 to Oct 2
$344 total
Oct 1 - Oct 2
Total with taxes and fees
Book a stay at this golf hotel in Windham. Enjoy free WiFi, free parking, and 2 bars/lounges. Popular attractions Windham Mountain Resort and Windham Country ...
Eastwind Windham
See all 2,192 properties in Windham
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.
Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts

Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts

Windham NY
Book a stay at this family-friendly vacation home in Windham. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Windham Mountain ...
10/10 Exceptional! (115 reviews)
"Very good rental"

Reviewed on Jul 26, 2026

Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts
Woodside Cabin #2 on Lake Heloise

Woodside Cabin #2 on Lake Heloise

Windham NY
Stay at this cabin in Windham. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions Windham Mountain Resort and Elm Ridge Wild Forest ...
9.4/10 Exceptional! (20 reviews)
"i love our stay, its like renting the whole compound. we came with our dog. the place is so relaxing."

Reviewed on Sep 14, 2026

Woodside Cabin #2 on Lake Heloise
Cutest Cabin in Windham on site miniature golfing with fire pit and BBQ

Cutest Cabin in Windham on site miniature golfing with fire pit and BBQ

Windham NY
Stay at this cabin in Windham. Enjoy free WiFi, a garden, and patios. Popular attractions Windham Mountain Resort and Windham Country Club are located ...
10/10 Exceptional! (75 reviews)
"It was very clean and a perfect place that we stayed for my birthday weekend"

Reviewed on Sep 22, 2026

Cutest Cabin in Windham on site miniature golfing with fire pit and BBQ
See all properties in Windham
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.

Stay near popular Windham attractions

Windham Mountain Resort

9.0/10 (313 reviews)
Hit the slopes in Windham with a visit to Windham Mountain Resort. Discover the mountain views in this relaxing area.
See properties

Frequently asked questions

Is Windham worth visiting?
Windham is worth visiting for its excellent outdoor recreation, including activities at Windham Mountain Resort and Windham Country Club. Travelers can also enjoy a variety of dining experiences, with options ranging from Italian to North American cuisine, offering diverse flavors for every palate.
When is the best time to visit Windham?
The best time to visit Windham is from May through September, when the weather is generally pleasant for outdoor activities. For fewer crowds and better value, consider visiting during the quieter months of November through February, which offer cooler temperatures and opportunities for snow.
What is Windham known for?
Windham is known for Windham Mountain Resort, a popular spot for outdoor activities, and Windham Country Club. Travelers can also explore the natural beauty of Elm Ridge Wild Forest and enjoy the local Italian food options available throughout the city.
What is a good itinerary length for Windham?
A good itinerary length for Windham is two to three days to enjoy Windham Mountain Resort, Windham Country Club, and Elm Ridge Wild Forest. For an extended stay of four to five days, travelers can add a Beginner Overnight Backpacking Adventure and more time for skiing or golf, experiencing all the area has to offer. See Windham Activities.
What are the top things to do in and around Windham?
Windham offers outdoor adventures, natural beauty, and unique local experiences for travelers:

  • Ski Windham Mountain Resort, a popular destination for winter sports.
  • Embark on a Beginner Overnight Backpacking Adventure.
  • Explore Elm Ridge Wild Forest, known for its natural landscapes.
  • Tour Windham Vineyards and Winery to sample local wines.
  • Hike Huntersfield State Forest, offering more natural beauty.

How do I plan a trip to Windham?
To plan your trip to Windham, search for hotels and book flights and rental cars in advance. Explore activities like a Beginner Overnight Backpacking Adventure or a Windham Mountain Ski Resort Day Trip. Visit Windham Mountain Resort or Elm Ridge Wild Forest, but always have indoor backup plans for outdoor activities.
What cuisines can you find in Windham?
In Windham you can find Mediterranean cuisine, with dishes like hummus, gyros, and falafel. Travelers also have options for Italian, North American, and Asian food, plus Latin American choices such as Mexican dishes. The area also offers coffee shops and speakeasy bars.
Can I book a refundable hotel in Windham?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Windham by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Windham with Expedia?
Expedia makes it easier to plan your Windham trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Windham?
The best choice depends on your travel style. Hotels in Windham can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Windham trip on Expedia?
Once you've booked your Windham trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Windham trip?
Expedia offers customer support before, during, and after your Windham trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Windham?
If it's your first trip to Windham, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Windham hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Windham hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

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