How much does a Windham vacation package cost?

You can pick up a vacation package to this destination from $418 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?

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. 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. 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. 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. 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. 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.

Windham Vacation Packages 2025/2026 from $605

The Latest Windham vacation packages

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

Hotel Vienna

Save 100% on your flight

per person

Oct 4 - Oct 8

found 1 day ago

Roundtrip flight included

Tampa (TPA) to Hudson (HCC)

9.4/10 Exceptional! (605 reviews)

Friendly staff , direct access to states trails.very nice !

Reviewed on Aug 16, 2025

AutoCamp Catskills

Save 100% on your flight

per person

Oct 2 - Oct 5

found 13 hours ago

Roundtrip flight included

Detroit (DTW) to Hudson (HCC)

9/10 Wonderful! (409 reviews)

It was good expensive overall, but they can do better

Reviewed on Aug 7, 2025

Hunter Lodge, a Bluebird by Lark

Save 100% on your flight

per person

Oct 2 - Oct 5

found 13 hours ago

Roundtrip flight included

Detroit (DTW) to Hudson (HCC)

9.2/10 Wonderful! (719 reviews)

Nice quiet place, very kind staff.

Reviewed on Aug 15, 2025

Game Farm Villa by Avantstay 10bdr, Private Pond, Spa, Pool Family-friendly

Save 100% on your flight

per person

Oct 2 - Oct 5

found 7 hours ago

Roundtrip non-stop flight included

Orlando (ORL) to Hudson (HCC)

No reviews

Cortland by Avantstay Charming Heritage Estate w/ Private Lake & Pool

Save 100% on your flight

per person

Oct 2 - Oct 5

found 13 hours ago

Roundtrip flight included

Detroit (DTW) to Hudson (HCC)

9/10 Wonderful! (2 reviews)

Fine, elegant, house. A great departure from one’s daily life. Great layout but could use more lighting. There were old quirks about the house but it made it more unique. Some doors don’t shut and will rattle when windows are open. Could use a griddle or larger pans/more baking sheets. The property is gorgeous and the crisp air was refreshing. Lovely experience and would book again!

Reviewed on Apr 7, 2024

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Windham Hotel Deals

Hotel Vienna

107 State Route 296, Windham, NY

Fully refundableReserve now, pay when you stay

$130 nightly

$140 total

Sep 8 - Sep 9

Total includes taxes and fees

9.2/10 Wonderful! (616 reviews)

"Great hotel"

Reviewed on Aug 12, 2025

Eastwind Windham

5088 NY-23, Windham, NY

$225 nightly

$243 total

Sep 1 - Sep 2

Total includes taxes and fees

9.2/10 Wonderful! (58 reviews)

"Friendly staff, accommodating and clean Some of it under construction"

Reviewed on May 23, 2025

Wylder Hotel Windham

19 New York 296, Windham, NY

$270 nightly

$292 total

Aug 19 - Aug 20

Total includes taxes and fees

8.6/10 Excellent! (67 reviews)

"We LOVED staying at Wylder. The staff was super friendly and helpful. Our room was comfortable, views were amazing and we really enjoyed the amenities. Highly recommend!"

Reviewed on Jul 21, 2025

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.

Things to do in and around Windham

Windham, New York, is the perfect destination for ski and adventure enthusiasts, offering a range of exciting activities. Visitors can enjoy skiing at the popular Windham Mountain Ski Resort, partake in weekend skiing, or explore various package and outdoor excursions. With its beautiful ski fields and adventure excursions, Windham promises an unforgettable vacation for sports lovers and nature seekers alike.

Shopping

For a delightful shopping experience in Windham, visit the Woodstock Music Shop for unique music gifts, located 20 miles away. If you're up for a drive, Vinnie's Farm Market, 17 miles away, offers fresh produce, while Hudson Valley Mall, 27 miles away, features diverse shops and entertainment options.

Recreation

Windham Country Club offers a scenic golf experience with outdoor vibes, perfect for sports enthusiasts. For a more tranquil retreat, Copperhood Retreat & Spa provides rejuvenating body treatments and a relaxing atmosphere, located a short drive away, ensuring a perfect blend of wellness and leisure.

Adventure

Windham Mountain Resort offers thrilling skiing experiences amidst stunning mountain scenery, perfect for adventure seekers. For a splash of fun, visit Zoom Flume, a family-friendly waterpark 7 miles away, featuring exciting rides and attractions. Don't miss the Zephyr Express Ski Lift, also 7 miles away, for breathtaking views and exhilarating slopes.

Nightlife

Windham offers a charming nightlife with cozy bars and live music venues. Start your evening at the Windham Mountain Resort's après-ski scene, then enjoy a laid-back drink at the Black Forest Inn, where the atmosphere is warm and inviting.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Windham

Windham, New York, is an ideal destination for skiing and adventure sports enthusiasts. Visitors can explore attractions like Windham Mountain, scenic waterfalls, and nearby state parks, all offering diverse outdoor experiences. Whether you're seeking thrilling adventures or a taste of local culture, Windham promises a memorable getaway for every traveler.

Windham Mountain Resort: Experience the thrill of winter sports at Windham Mountain Resort, where skiing and snowboarding meet breathtaking mountain scenery. This resort offers diverse terrain for all skill levels, along with year-round outdoor adventures like mountain biking and hiking, perfect for those seeking a lively outdoor atmosphere.
Kaaterskill Falls: A stunning 260-foot waterfall located 12 miles from Windham, Kaaterskill Falls is an iconic natural wonder. The picturesque hike to the falls enhances its romantic and adventurous vibe, making it a perfect spot for nature lovers and photographers alike.
Mountain Top Arboretum: Situated 8 miles away, the Mountain Top Arboretum features beautifully landscaped gardens and diverse plant collections. This serene outdoor space is ideal for family outings, offering educational opportunities and peaceful trails to explore the beauty of nature.

Best time to go to Windham

The best time to visit Windham is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly high and weather is mostly with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	22.1°F (-5.5°C)	Light Rain	Mostly	Slightly High	Average
February	24.1°F (-4.4°C)	Light Rain	Mostly	Slightly High	Average
March	31.6°F (-0.2°C)	Light Rain	Mostly	Average	Slightly Low
April	43.3°F (6.3°C)	Light Rain	Mostly	Average	Slightly Low
May	55.6°F (13.1°C)	Light Rain	Mostly Sunny	Slightly Low	Average
June	63.0°F (17.2°C)	Light Rain	Mostly Sunny	Slightly Low	Average
July	68.7°F (20.4°C)	Light Rain	Mostly Sunny	Average	Slightly High
August	66.7°F (19.3°C)	Light Rain	Mostly Sunny	Average	Slightly High
September	59.9°F (15.5°C)	Light Rain	Mostly Sunny	Average	Average
October	48.9°F (9.4°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly High
November	36.7°F (2.6°C)	Light Rain	Mostly Sunny	Average	Slightly Low
December	28.8°F (-1.8°C)	Light Rain	Mostly	Slightly High	Average

Tips to save on your trip to Windham

Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Windham.
Consider traveling to Windham during the low season (March to April and November) for more affordable options.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.