Windham Holidays

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Windham Holiday

Windham Essential Information

Language
English
Currency
U.S dollars
Population
370
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Hunter Mountain, Zoom Flume and Blackhead Mountain Country Club

Our pick of the best Windham Hotel Deals

Hotel Vienna

Hotel Vienna

3 out of 5
107 State Route 296 Windham NY
Fully refundableReserve now, pay when you stay
The price is AU$198 per night from 2 Nov to 3 Nov
AU$198
2 Nov - 3 Nov
includes taxes & fees
9.4/10 Exceptional! (899 reviews)
"Breakfast room needs to more spacious and good handle electrical devices like , micro oven , toaster , .. that would be more efficient for the environment. Thank you"

Reviewed on 29 Oct 2026

Hotel Vienna
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
19 New York 296 Windham NY
The price is AU$275 per night from 31 Oct to 1 Nov
AU$275
31 Oct - 1 Nov
includes taxes & fees
9/10 Wonderful! (134 reviews)
"El personal de recepcion fue muy atento y servicial. Nos encanto todas las amenidades del hotel y la energia del sitio. Definitavemente queremos volver."

Reviewed on 26 Oct 2026

Wylder Hotel Windham
The Winwood Condominiums

The Winwood Condominiums

3 out of 5
5220 NY-23 Windham NY
The price is AU$259 per night from 1 Nov to 2 Nov
AU$259
1 Nov - 2 Nov
includes taxes & fees
8.8/10 Excellent! (372 reviews)
"Such a cute and clean condo with friendly, helpful staff. Peaceful location close to Catskill and ski slopes."

Reviewed on 25 Oct 2026

The Winwood Condominiums
See all 2,178 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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