Windham Vacation Packages

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Top Windham Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Kaatskill Mountain Club at Hunter Mountain

Kaatskill Mountain Club at Hunter Mountain

2 out of 5
Price was CA $851, price is now CA $744 per person
CA $744
per person
Oct 2 - Oct 5
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Hudson (HCC)
9.2/10 Wonderful! (266 reviews)
Very convenient to hiking trails. Staff very friendly and helpful

Reviewed on Aug. 23, 2025

AutoCamp Catskills

AutoCamp Catskills

5 out of 5
Price was CA $1,417, price is now CA $1,087 per person
CA $1,087
per person
Oct 2 - Oct 5
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Hudson (HCC)
9/10 Wonderful! (411 reviews)
It was good expensive overall, but they can do better

Reviewed on Aug. 7, 2025

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

3 out of 5
Price was CA $1,043, price is now CA $906 per person
CA $906
per person
Oct 2 - Oct 5
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Hudson (HCC)
9.2/10 Wonderful! (737 reviews)
Comfortable, clean room. Beautiful surroundings. Friendly, helpful staff.

Reviewed on Aug. 23, 2025

Couple s Oasis Pool Stream Firepit Steam Room

Couple s Oasis Pool Stream Firepit Steam Room

2 out of 5
Price was CA $1,367, price is now CA $1,252 per person
CA $1,252
per person
Oct 2 - Oct 5
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Hudson (HCC)
No reviews
Overlook Hotel

Overlook Hotel

2 out of 5
Price was CA $1,093, price is now CA $1,011 per person
CA $1,011
per person
Oct 2 - Oct 5
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Hudson (HCC)
7.8/10 Good! (7 reviews)

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Windham Hotel Deals

Hotel Vienna

Hotel Vienna

2.5 out of 5
107 State Route 296, Windham, NY
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from Sep 25 to Sep 26
CA $167
CA $181 total
Sep 25 - Sep 26
includes taxes & fees
9.2/10 Wonderful! (621 reviews)
Nice surprise!
"What a nice surprise the Hotel Vienna turned out to be! I highly recommend it if you're visiting the Catskills. It had what we were looking for: an easy to moderate hike, an indoor heated swimming pool, great selection of cable TV channels and clean, clean, clean."

Reviewed on Aug. 21, 2025

Hotel Vienna
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
19 New York 296, Windham, NY
The price is CA $263 per night from Aug 26 to Aug 27
CA $263
CA $354 total
Aug 26 - Aug 27
includes taxes & fees
8.6/10 Excellent! (69 reviews)
"Quick and friendly"

Reviewed on Aug. 18, 2025

Wylder Hotel Windham
Eastwind Windham

Eastwind Windham

2 out of 5
5088 NY-23, Windham, NY
The price is CA $275 per night from Aug 26 to Aug 27
CA $275
CA $307 total
Aug 26 - Aug 27
includes taxes & fees
9.2/10 Wonderful! (59 reviews)
"Friendly staff, accommodating and clean Some of it under construction"

Reviewed on May 23, 2025

Eastwind 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.
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Discover the most popular places to visit in Windham

Windham Mountain Resort

Hit the slopes in Windham with a visit to Windham Mountain Resort. Discover the mountain views in this relaxing area.

Windham Mountain Resort

Frequently asked questions

How much does a Windham vacation package cost?
You'll find cheap prices from CA $744 on Expedia for your Windham break. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your vacation to Windham costs.
What are the cheapest months to go to Windham?
You can generally find lower rates and greater availability in March, April and November. Check out our cheap Windham vacation packages and you could score some great off-season discounts.
How many days is enough for Windham?
With a well-planned itinerary, you can easily visit the main Windham sights in a few days. But if you want to venture off the beaten track or go on day tours, think about booking your Windham vacation for longer.
How to find the best Windham package deals?
Use Expedia's filter tool to find some terrific Windham package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Windham package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Windham vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component separately. And you'll still have the flexibility to create a tailored Windham vacation by choosing your preferred airline, accommodation type and car class.
How to plan a trip to Windham?

  1. Choose when to go: Check your schedule and get packing. Your favourite season and the available activities will also help you decide when to vacation in Windham.
  2. Plan your budget wisely: Besides the cost of your hotel, you should factor in other expenses too. These include flights, food and transportation. Also, put aside some extra funds for unexpected costs that could crop up during your trip to Windham.
  3. Set the duration of your trip: Start by compiling a list of the sights and activities you'd like to get to in Windham. Then, estimate how long you'll need at each, along with any travel time.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to pick a Windham vacation package that brings all your bookings together.

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