Windham Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Windham

Hotel Vienna

Hotel Vienna

2.5 out of 5
107 State Route 296, Windham, NY
9.2/10 Wonderful! (618 reviews)
"Hotel was very clean, grounds looked great and the owner/manager was constantly waiting on guests."

Reviewed on 16 Aug 2025

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Hotel Vienna
Eastwind Windham

Eastwind Windham

2 out of 5
5088 NY-23, Windham, NY
The price is 5.822.014 ₫ per night from 1 Sept to 2 Sept
5.822.014 ₫
6.491.545 ₫ total
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (59 reviews)
"Friendly staff, accommodating and clean Some of it under construction"

Reviewed on 23 May 2025

Eastwind Windham
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
19 New York 296, Windham, NY
The price is 5.023.661 ₫ per night from 27 Aug to 28 Aug
5.023.661 ₫
6.744.203 ₫ total
27 Aug - 28 Aug
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 21 Jul 2025

Wylder Hotel 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.

Frequently asked questions

How much does a Windham holiday package cost?
You can pick up a holiday package to this destination on Expedia. But how much your holiday 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 holiday package, consider travelling 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 holiday 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 personalise 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 travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Windham holiday as a package?
Expedia holiday 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 holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday 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 favourite 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 accommodation: After you've nailed down your dates and duration, lock in the right Windham holiday package for you.