Windham Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Ready to book your vacation to Windham?

 

Choose your dates

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 $179 per night from Sep 8 to Sep 9
CA $179
CA $193 total
Sep 8 - Sep 9
includes taxes & fees
9.2/10 Wonderful! (616 reviews)
"Great hotel"

Reviewed on Aug. 12, 2025

Hotel Vienna
Eastwind Windham

Eastwind Windham

2 out of 5
5088 NY-23, Windham, NY
The price is CA $275 per night from Aug 19 to Aug 20
CA $275
CA $307 total
Aug 19 - Aug 20
includes taxes & fees
9.2/10 Wonderful! (58 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 $263 per night from Aug 19 to Aug 20
CA $263
CA $353 total
Aug 19 - Aug 20
includes taxes & fees
8.6/10 Excellent! (67 reviews)
"We LOVED staying at Wylder. The staff was super friendly and helpful. Our room was comfortable, views were amazing and we really enjoyed the amenities. Highly recommend!"

Reviewed on Jul. 21, 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

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.