Windham Vacations
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Find the Best Windham Vacation Packages
Windham Hotel Deals
Wylder Hotel Windham
19 New York 296 Windham NY
￥34,755
￥45,499 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (115 reviews)
"The staff were wonderful and went out of their way to make sure you had whatever you wanted. There are plenty of things to do right at the hotel and you are right by the mountains if you want to take advantage of that. The pool is heated and you can have drinks by the pool. There are several locations ..."
Reviewed on Aug 9, 2026
Hotel Vienna
107 State Route 296 Windham NY
Fully refundableReserve now, pay when you stay
￥20,644
￥25,050 total
Aug 18 - Aug 19
includes taxes & fees
9.4/10 Exceptional! (841 reviews)
"the back decks and the path"
Reviewed on Aug 12, 2026
Eastwind Windham
5088 NY-23 Windham NY
￥28,793
￥35,544 total
Aug 17 - Aug 18
includes taxes & fees
9.2/10 Wonderful! (113 reviews)
"Excellence as always — can’t wait to come back."
Reviewed on Aug 11, 2026
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)
This four-season Catskills resort offers 54 trails across 285 skiable acres for all ability levels. Experience winter's pristine slopes or summer's mountain biking and golf on the championship course.
Windham Country Club
8.4/10 (20 reviews)
Nestled in the Great Northern Catskills, Windham Country Club features an 18-hole course with mountain views and stream-side fairways. After your round, unwind at Mulligan's Pub with panoramic vistas of the peaks.
Windham Vineyards and Winery
9.0/10 (15 reviews)
Nestled in the Catskills, The Vineyard at Windham offers tastings from New York's finest wine regions. Savor diverse selections on their outdoor terrace while taking in spectacular Windham Mountain views.
Huntersfield State Forest
This serene 1,300-acre forest offers a mix of evergreen plantations and northern hardwood trees. Hike the designated trail to the summit lean-to for panoramic views of the majestic Catskill Mountains.
Elm Ridge Wild Forest
Commune with nature and explore the great outdoors at Elm Ridge Wild Forest during your travels in Windham. Discover the mountain views and coffeehouses in this relaxing area.
Ashland Park
This serene community park offers peaceful green spaces perfect for picnics and casual strolls. Enjoy a quiet retreat in nature, where locals gather for leisure activities away from the bustle of everyday life.
What to do in Windham
Frequently asked questions
How much does a Windham vacation package cost?
You can pick up a vacation package to this destination on Expedia. But how much your vacation to Windham costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Windham?
If you'd like to score a cheap Windham vacation package, consider traveling in March, April and November. You'll generally find better prices on hotels and flights during these quieter months — ideal for a budget-friendly break.
How many days is enough for Windham?
The ideal length of your Windham vacation depends on what you'd like to do. Typically, a handful of days to a week will give you enough time to hit all the leading sights and explore some hidden spots along the way.
How to find the best Windham package deals?
Bagging a cheap Windham package deal is a cinch with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, add some filters and see what's available. You can personalize your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most affordable Windham package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book a Windham vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component individually. And you'll still have the flexibility to create a tailored Windham vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Windham?
If you're planning a spur-of-the-moment Windham adventure, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land amazing deals on your hotels and flights by booking ahead.
How to plan a trip to Windham?
- Choose your travel dates: What you want to do in Windham and your favorite season will help you decide when to travel.
- Plan your budget wisely: As well as the price of your stay, you'll need to factor in other expenses too. These include food, transportation and flights. Also, set aside a little extra for unexpected costs that could crop up during your trip to Windham.
- Decide your trip length: Think about how long you'd like to spend discovering Windham. Plan your days so you can get to all the activities and attractions you're interested in without rushing.
- Bundle your airfare and accommodations: After you've nailed down your dates and duration, lock in the right Windham vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
