Windham Vacations

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to ￥45,448 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Find the Best Windham Vacation Packages

Windham Hotel Deals

Hotel Vienna

Hotel Vienna

2.5 out of 5
107 State Route 296, Windham, NY
9.2/10 Wonderful! (622 reviews)
Nice surprise!
"What a nice surprise the Hotel Vienna turned out to be! I highly recommend it if you're visiting the Catskills. It had what we were looking for: an easy to moderate hike, an indoor heated swimming pool, great selection of cable TV channels and clean, clean, clean."

Reviewed on Aug 21, 2025

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Hotel Vienna
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
19 New York 296, Windham, NY
The price is ￥31,471 per night from Aug 31 to Sep 1
￥31,471
￥41,362 total
Aug 31 - Sep 1
includes taxes & fees
8.6/10 Excellent! (69 reviews)
"Quick and friendly"

Reviewed on Aug 18, 2025

Wylder Hotel Windham
Eastwind Windham

Eastwind Windham

2 out of 5
5088 NY-23, Windham, NY
The price is ￥49,815 per night from Aug 29 to Aug 30
￥49,815
￥55,545 total
Aug 29 - Aug 30
includes taxes & fees
9.2/10 Wonderful! (59 reviews)
"Friendly staff, accommodating and clean Some of it under construction"

Reviewed on May 23, 2025

Eastwind Windham
See all 2,074 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.

What to do in Windham

Windham Transportation Only from NYC

Windham Transportation Only from NYC

￥10,198
per adult
Windham Transportation Only from NYC
See all activities 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?

  1. Choose your travel dates: What you want to do in Windham and your favorite season will help you decide when to travel.
  2. 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.
  3. 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.
  4. 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.