Windham Vacations

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Discover the most popular places to visit in Windham

Windham Mountain Resort

4.5/5(89 reviews)

Hit the slopes in Windham with a visit to Windham Mountain Resort. Discover the mountain views in this relaxing area.

Windham Mountain Resort

Windham Country Club

4.5/5(3 reviews)

Enjoy a round of golf in Windham at Windham Country Club. Discover the mountain views in this relaxing area.

Windham Country Club

Windham Hotel Deals

Hotel Vienna

Hotel Vienna

2.5 out of 5
107 State Route 296, Windham, NY
$110 nightly
The price is $119 total per night from Nov 18 to Nov 19
$119 total
Nov 18 - Nov 19
Total with taxes and fees
9.2/10 Wonderful! (667 reviews)
"Beautiful hotel"

Reviewed on Oct 16, 2025

Hotel Vienna
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
19 New York 296, Windham, NY
$234 nightly
The price is $253 total per night from Oct 22 to Oct 23
$253 total
Oct 22 - Oct 23
Total with taxes and fees
8.6/10 Excellent! (74 reviews)
"The property was very nice. The staff was very friendly and accommodating. Overall our stay was great. My only complaint would be the inconvenience about morning coffee. There is no coffee pot in the rooms and no coffee in the lobby. You have to walk to another building to a bakery to purchase coffee ..."

Reviewed on Oct 13, 2025

Wylder Hotel Windham
Eastwind Windham

Eastwind Windham

2 out of 5
5088 NY-23, Windham, NY
$173 nightly
The price is $187 total per night from Nov 6 to Nov 7
$187 total
Nov 6 - Nov 7
Total with taxes and fees
9.2/10 Wonderful! (63 reviews)
"Friendly staff, accommodating and clean Some of it under construction"

Reviewed on May 23, 2025

Eastwind Windham
See all 2,077 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.

Find the Best Windham Vacation Packages

Windham Essential Information

Language
English
Currency
U.S dollars
Population
370
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Hunter Mountain, Zoom Flume and Blackhead Mountain Country Club

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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?
You can usually find reduced prices and better availability in April, May and October. Browse our cheap Windham vacation packages and you could get some great off-season deals.
How many days is enough for Windham?
With a well-organized itinerary, you can easily visit the most popular Windham attractions in a handful of days. But if you'd like to discover hidden gems or take day trips, think about booking your Windham vacation for longer.
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. Pick the ideal time to travel: Your schedule, favorite season and the type of weather you enjoy can all impact your decision on when to travel to Windham.
  2. Work out your budget: Make sure you have enough money to cover everything from meals and transportation to activities and flights. Your accommodations will probably be the largest expense during your trip to Windham.
  3. Explore Windham with Expedia's trip planning tool: Gain insights into the most popular attractions and best hotels for your trip to Windham. You can also save your favorite locations, collaborate with your group and manage all your plans in one place.
  4. Decide how long to go away for: Now that you're more familiar with Windham, you can figure out the perfect length of your break. Pull together a draft plan and allocate enough time to get through everything on your must-do list.
  5. Bundle your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to pick a Windham vacation package that brings all your bookings together.
  6. Book experiences or activities ahead of time: Whether it's a ticket to a big attraction or a walking tour, you won't have to worry about missing out on Windham's best offerings. Find all the fun things to do in Windham with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Windham vacation packages?
If you're anything like us, you love traveling the world but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the overall cost of your Windham break across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up great vacation packages with payment plans as soon as you spot them.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.