Windham Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Windham

Hotel Vienna

Hotel Vienna

3 out of 5
107 State Route 296 Windham NY
Fully refundableReserve now, pay when you stay
The price is 3.737.593 ₫ per night from 28 Jul to 29 Jul
3.737.593 ₫
4.491.265 ₫ total
28 Jul - 29 Jul
includes taxes & fees
9.4/10 Exceptional! (822 reviews)
"The property was super clean , friendly staff and great amenities! Can wait to get back there ."

Reviewed on 5 Jul 2026

Hotel Vienna
Eastwind Windham

Eastwind Windham

3.5 out of 5
5088 NY-23 Windham NY
The price is 5.693.826 ₫ per night from 27 Jul to 28 Jul
5.693.826 ₫
6.916.636 ₫ total
27 Jul - 28 Jul
includes taxes & fees
9.2/10 Wonderful! (107 reviews)
"Beautiful location. Really loved the full window ceiling in the cabin’s shower!"

Reviewed on 19 Jun 2026

Eastwind Windham
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
19 New York 296 Windham NY
The price is 5.790.719 ₫ per night from 23 Jul to 24 Jul
5.790.719 ₫
7.568.827 ₫ total
23 Jul - 24 Jul
includes taxes & fees
8.8/10 Excellent! (101 reviews)
"Our stay was ok. The staff was very responsive when we contacted the front desk, however we tried not to complain when things were not done or not working. The pool was lovely, however staff were power washing the fences on two days when the pool was open! Why this wasn't done in the Spring is suprising.The ..."

Reviewed on 5 Jul 2026

Wylder Hotel Windham
See all 2,172 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.

Stay near popular Windham attractions

Windham Mountain Resort

9.0/10 (313 reviews)
This four-season Catskills resort offers 54 trails across 285 skiable acres for all ability levels. Experience winter's pristine slopes or summer's mountain biking and golf on the championship course.
See properties

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.

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