Windham Packages (Flight + Hotel)

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Top hotels in Windham

Hotel Vienna

Hotel Vienna

3 out of 5
107 State Route 296 Windham NY
The price is ฿4,458 per night from 9 Aug to 10 Aug
฿4,458
฿5,393 total
9 Aug - 10 Aug
includes taxes & fees
9.4/10 Exceptional! (826 reviews)
"Hotel Vienna is awesome! Family Friendly.. pet friendly…. Staff great! Fun to have Suana this time with pool… miss not having the hot tub…. 💙🧡💜❤️"

Reviewed on 11 Jul 2026

Hotel Vienna
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
19 New York 296 Windham NY
The price is ฿6,635 per night from 20 Jul to 21 Jul
฿6,635
฿8,840 total
20 Jul - 21 Jul
includes taxes & fees
8.8/10 Excellent! (104 reviews)
"Gorgeous property, photos don’t do it justice. Perfect getaway. We had the best time! Sauna, swimming in the nearby creek, fire pits, pool time, so much greenery, and a great bakery! Country vibe- not a modern feel- like glamorous summer camp. We loved it!"

Reviewed on 15 Jul 2026

Wylder Hotel Windham
Eastwind Windham

Eastwind Windham

3.5 out of 5
5088 NY-23 Windham NY
The price is ฿7,250 per night from 11 Aug to 12 Aug
฿7,250
฿8,807 total
11 Aug - 12 Aug
includes taxes & fees
9.2/10 Wonderful! (111 reviews)
"The place is perfect for couples, very quiet and relaxing. The cabin was clean and well mantained, the property has bikes that you can use. They welcome you with a smores kit. I recommend this place a lot!"

Reviewed on 13 Jul 2026

Eastwind Windham
See all 2,158 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

What to do in Windham

Windham Transportation Only from NYC

Windham Transportation Only from NYC

฿2,267
per adult
Windham Transportation Only from NYC
Round Trip Transport to Hunter Mountain

Transport to Hunter Mountain

฿2,267
per adult
Transport to Hunter Mountain
See all activities in Windham

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.

Explore a world of travel with Expedia

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