Windham Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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Ready to book your vacation to Windham?

 

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Windham Hotel Deals

Hotel Vienna
Hotel Vienna
2.5 out of 5
107 State Route 296, Windham, NY
Fully refundableReserve now, pay when you stay
The price is CA $170 per night from Jul 6 to Jul 7
CA $170
CA $184 total
Jul 6 - Jul 7
includes taxes & fees
9.2/10 Wonderful! (580 reviews)
"Wonderful place, I love it and and definitely recommend."

Reviewed on Jun. 30, 2025

Hotel Vienna
Eastwind Windham
Eastwind Windham
2 out of 5
5088 NY-23, Windham, NY
The price is CA $271 per night from Jul 6 to Jul 7
CA $271
CA $302 total
Jul 6 - Jul 7
includes taxes & fees
9.2/10 Wonderful! (56 reviews)
"Friendly staff, accommodating and clean Some of it under construction"

Reviewed on May 23, 2025

Eastwind Windham
Wylder Hotel Windham
Wylder Hotel Windham
3.5 out of 5
19 New York 296, Windham, NY
The price is CA $231 per night from Jul 7 to Jul 8
CA $231
CA $317 total
Jul 7 - Jul 8
includes taxes & fees
8.4/10 Very Good! (60 reviews)
"Great!"

Reviewed on Jun. 30, 2025

Wylder Hotel 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.

Discover the most popular places to visit in Windham

What to do in Windham

Frequently asked questions

How much does a Windham vacation package cost?
You'll find cheap prices on Expedia for your Windham break. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your vacation to Windham costs.
What are the cheapest months to go to Windham?
You can generally find lower rates and greater availability in March, April and November. Check out our cheap Windham vacation packages and you could score some great off-season discounts.
How many days is enough for Windham?
With a well-planned itinerary, you can easily visit the main Windham sights in a few days. But if you want to venture off the beaten track or go on day tours, think about booking your Windham vacation for longer.
How to find the best Windham package deals?
Use Expedia's filter tool to find some terrific Windham package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Windham package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
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 flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component separately. And you'll still have the flexibility to create a tailored Windham vacation by choosing your preferred airline, accommodation type and car class.
How to plan a trip to Windham?

  1. Choose when to go: Check your schedule and get packing. Your favourite season and the available activities will also help you decide when to vacation in Windham.
  2. Plan your budget wisely: Besides the cost of your hotel, you should factor in other expenses too. These include flights, food and transportation. Also, put aside some extra funds for unexpected costs that could crop up during your trip to Windham.
  3. Set the duration of your trip: Start by compiling a list of the sights and activities you'd like to get to in Windham. Then, estimate how long you'll need at each, along with any travel time.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to pick a Windham vacation package that brings all your bookings together.

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