Windham Vacations from $209

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The Latest Windham vacation packages

Price found within the past 48 hours. Click for updated prices.
SunView Motel

SunView Motel

2.5 out of 5
per person
Aug 4 - Aug 6
found 11 hours ago
Roundtrip flight included
Cleveland (CLE) to Hudson (HCC)
8.6/10 Excellent! (536 reviews)
This place is, in the best possible way, a blast from the past! A nice, quaint roadside motel with a mountain vibe! Great views of the Catskills from the small hill where there’s a fire pit and Adirondack chairs for relaxation and lounging. Re-read Rip Van Winkle after a fantastic dinner at Deer Mountain Inn as it got dark looking upon the mountains where the story took place. Picturesque and perfect! Had the entire motel to myself and it was so nice, quiet, peaceful and relaxing. Wonderful experience!

Reviewed on Jun 16, 2025

AutoCamp Catskills

AutoCamp Catskills

5 out of 5
per person
Aug 4 - Aug 6
found 11 hours ago
Roundtrip flight included
Cleveland (CLE) to Hudson (HCC)
9/10 Wonderful! (399 reviews)
I enjoyed the common space/lodge. It poured during our stay, so it was good to have a dry space to gather with the friends that we went with. I disliked that there were limited activities for children. A larger playground, pool or splash pad would be nice additions.

Reviewed on Jun 30, 2025

Clove by Avantstay Gorgeous Cottage w/ Pool, Privacy, Pool Table & Close to Hunter Mountain

Clove by Avantstay Gorgeous Cottage w/ Pool, Privacy, Pool Table & Close to Hunter Mountain

3.5 out of 5
Save 100% on your flight
per person
Aug 4 - Aug 6
found 11 hours ago
Roundtrip flight included
Cleveland (CLE) to Hudson (HCC)
No reviews
The Herwood Inn

The Herwood Inn

4.5 out of 5
per person
Aug 4 - Aug 6
found 11 hours ago
Roundtrip flight included
Cleveland (CLE) to Hudson (HCC)
9.8/10 Exceptional! (76 reviews)
Really comfortable, well maintained property. Very modern appliances, well thought out. Whole place is VERY MODERN. I loved it.

Reviewed on Jun 27, 2025

Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
per person
Aug 4 - Aug 6
found 11 hours ago
Roundtrip flight included
Cleveland (CLE) to Hudson (HCC)
9.4/10 Exceptional! (156 reviews)
Stunning room. Great amenities including a very cool turntable with a choice of albums from the 60s. Really nice balcony too.

Reviewed on Jun 29, 2025

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Discover the most popular places to visit in Windham

Windham Mountain Resort

4.5/5(89 reviews)

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

Windham Mountain Resort

Windham Country Club

4.5/5(3 reviews)

Enjoy a round of golf in Windham at Windham Country Club. Discover the mountain views in this relaxing area.

Windham Country Club

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
$122 nightly
The price is $132 total per night from Jul 6 to Jul 7
$132 total
Jul 6 - Jul 7
Total includes taxes and fees
9.2/10 Wonderful! (580 reviews)
"Wonderful place, I love it and and definitely recommend."

Reviewed on Jun 30, 2025

Hotel Vienna
Eastwind Windham
Eastwind Windham
2 out of 5
5088 NY-23, Windham, NY
$229 nightly
The price is $247 total per night from Jul 6 to Jul 7
$247 total
Jul 6 - Jul 7
Total includes taxes and fees
9.2/10 Wonderful! (56 reviews)
"Friendly staff, accommodating and clean Some of it under construction"

Reviewed on May 23, 2025

Eastwind Windham
Wylder Hotel Windham
Wylder Hotel Windham
3.5 out of 5
19 New York 296, Windham, NY
$216 nightly
The price is $234 total per night from Jul 7 to Jul 8
$234 total
Jul 7 - Jul 8
Total includes taxes and fees
8.4/10 Very Good! (60 reviews)
"Great!"

Reviewed on Jun 30, 2025

Wylder Hotel Windham
See all 2,059 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.

Find the Best Windham Vacation Packages

Windham Essential Information

Language
English
Currency
U.S dollars
Population
370
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Hunter Mountain, Zoom Flume and Blackhead Mountain Country Club

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Frequently asked questions

How much does a Windham vacation package cost?
You can pick up a vacation package to this destination from $209 on Expedia. But how much your vacation 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?
You can usually find reduced prices and better availability in April, May and October. Browse our cheap Windham vacation packages and you could get some great off-season deals.
How many days is enough for Windham?
With a well-organized itinerary, you can easily visit the most popular Windham attractions in a handful of days. But if you'd like to discover hidden gems or take day trips, think about booking your Windham vacation for longer.
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 personalize 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 traveling on a weekday, when prices are generally lower.
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 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 vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation 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. Pick the ideal time to travel: Your schedule, favorite season and the type of weather you enjoy can all impact your decision on when to travel to Windham.
  2. Work out your budget: Make sure you have enough money to cover everything from meals and transportation to activities and flights. Your accommodations will probably be the largest expense during your trip to Windham.
  3. Explore Windham with Expedia's trip planning tool: Gain insights into the most popular attractions and best hotels for your trip to Windham. You can also save your favorite locations, collaborate with your group and manage all your plans in one place.
  4. Decide how long to go away for: Now that you're more familiar with Windham, you can figure out the perfect length of your break. Pull together a draft plan and allocate enough time to get through everything on your must-do list.
  5. Bundle your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to pick a Windham vacation package that brings all your bookings together.
  6. Book experiences or activities ahead of time: Whether it's a ticket to a big attraction or a walking tour, you won't have to worry about missing out on Windham's best offerings. Find all the fun things to do in Windham with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Windham vacation packages?
If you're anything like us, you love traveling the world but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the overall cost of your Windham break across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.