Windham Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Top hotels in Windham

Hotel Vienna
Hotel Vienna
2.5 out of 5
107 State Route 296, Windham, NY
9.2/10 Wonderful! (553 reviews)
"Wow, what an incredible surprise! I wish I could have extended my stay. Holly at the front desk was incredibly kind, so thank you for making our trip even better!! The facilities were great: not only was the pool pristine, but there was also a sauna outside! There is also a path on the property which ..."

Reviewed on 21 Mar, 2025

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Hotel Vienna
Wylder Hotel Windham
Wylder Hotel Windham
3.5 out of 5
19 New York 296, Windham, NY
Fully refundableReserve now, pay when you stay
The price is S$407 per night from 14 Apr to 15 Apr
S$407
includes taxes & fees
14 Apr - 15 Apr
8.2/10 Very Good! (54 reviews)
"Family trip for snowboarding and was enjoyable setting. Enjoyed the firepit and s’mores."

Reviewed on 30 Mar, 2025

Wylder Hotel Windham
Eastwind Windham
Eastwind Windham
2 out of 5
5088 NY-23, Windham, NY
The price is S$288 per night from 6 Apr to 7 Apr
S$288
includes taxes & fees
6 Apr - 7 Apr
9.2/10 Wonderful! (50 reviews)
"Very lo-fi and bare bones, but well-designed and properly thought-out. Just what city hipster ski bums are looking for."

Reviewed on 16 Mar, 2025

Eastwind Windham
See all 1,994 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.