Windham Vacation Packages 2026 from $603

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The Latest Windham vacation packages

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

Hotel Vienna

$603

per person

Nov 20 - Nov 22

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Hudson (HCC)

9.4/10 Exceptional! (878 reviews)

Wylder Hotel Windham

$650

per person

Nov 20 - Nov 22

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Hudson (HCC)

8.8/10 Excellent! (128 reviews)

Clean and comfortable, but No heater , it was so cold. No free wifi .

Reviewed on Oct 19, 2026

The Haüs Windham

$844

per person

Nov 20 - Nov 22

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Hudson (HCC)

7.8/10 Good! (35 reviews)

Definitely see this place its great

Reviewed on Oct 16, 2026

Eastwind Windham

$668

per person

Nov 20 - Nov 22

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Hudson (HCC)

9.2/10 Wonderful! (120 reviews)

Loved the stay here as well as the friendly staff. Jamie who had helped us check in was very friendly, helpful and made us feel welcome. Location was very dog friendly. Our room was very clean, quiet and had a beautiful scene of nature. Nice place to choose for a quiet get away stay.

Reviewed on Oct 20, 2026

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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.

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Windham Country Club

8.4/10 (20 reviews)

Nestled in the Great Northern Catskills, Windham Country Club features an 18-hole course with mountain views and stream-side fairways. After your round, unwind at Mulligan's Pub with panoramic vistas of the peaks.

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Windham Vineyards and Winery

9.0/10 (15 reviews)

Nestled in the Catskills, The Vineyard at Windham offers tastings from New York's finest wine regions. Savor diverse selections on their outdoor terrace while taking in spectacular Windham Mountain views.

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Huntersfield State Forest

This serene 1,300-acre forest offers a mix of evergreen plantations and northern hardwood trees. Hike the designated trail to the summit lean-to for panoramic views of the majestic Catskill Mountains.

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Elm Ridge Wild Forest

Commune with nature and explore the great outdoors at Elm Ridge Wild Forest during your travels in Windham. Discover the mountain views and coffeehouses in this relaxing area.

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Ashland Park

This serene community park offers peaceful green spaces perfect for picnics and casual strolls. Enjoy a quiet retreat in nature, where locals gather for leisure activities away from the bustle of everyday life.

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Windham Hotel Deals

Hotel Vienna

107 State Route 296 Windham NY

$145 nightly

$157 total

Oct 21 - Oct 22

Total with taxes and fees

Wylder Hotel Windham

19 New York 296 Windham NY

$225 nightly

$243 total

Oct 30 - Oct 31

Total with taxes and fees

8.8/10 Excellent! (133 reviews)

"Clean and comfortable, but No heater , it was so cold. No free wifi ."

Reviewed on Oct 19, 2026

The Winwood Condominiums

5220 NY-23 Windham NY

$167 nightly

$180 total

Oct 21 - Oct 22

Total with taxes and fees

8.8/10 Excellent! (369 reviews)

"Winwood is an excellent choice if you’re looking to explore the Catskills! It is located just up the road from amazing restaurants and shops in Windham. The staff is amazing. There are so many amenities for adults and kids. 10/10 recommendation!"

Reviewed on Oct 18, 2026

See all 2,169 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

Things to do in and around Windham

Windham, New York, is an ideal destination for ski and adventure enthusiasts. Visitors can enjoy activities like skiing at Windham Mountain, exploring the ski resort, and participating in weekend skiing and various outdoor excursions. Additionally, adventure package excursions offer thrilling experiences for those looking to explore the beautiful surroundings. Whether you're a seasoned skier or a weekend warrior, Windham promises an exciting getaway.

Shopping

In Windham, you can find unique gifts at the Woodstock Music Shop, located 20 miles away. For fresh produce and local goods, visit Vinnie’s Farm Market, 17 miles from Windham. If you're up for a drive, check out Hudson Valley Mall, 27 miles away, offering a variety of shopping and entertainment options.

Recreation

Enjoy a round of golf at Windham Country Club, where you can embrace the outdoor vibes and beautiful scenery. For a nearby option, Thunderhart Golf Course offers a similar experience just 13 miles away. For ultimate relaxation, visit Copperhood Retreat & Spa, located 15 miles from Windham, for rejuvenating body treatments.

Adventure

Experience thrilling skiing at Windham Mountain Resort, where adventure meets the slopes. For water fun, visit Zoom Flume, a family-friendly waterpark located 7 miles away. Don’t miss the Zephyr Express Ski Lift, offering breathtaking views and exciting rides, also located 7 miles from Windham.

Nightlife

Windham's nightlife offers a cozy mountain vibe with local bars and live music. Check out The Windham Tavern for hearty pub fare and craft beers. For a laid-back evening, visit the Catskill Mountain Country Store, where you can enjoy local snacks and mingling with fellow travelers.

*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 ski and adventure enthusiasts, offering attractions like Windham Mountain, scenic waterfalls, and nearby national and state parks. Whether you're seeking outdoor thrills or a cultural experience, Windham caters to all types of travelers with its breathtaking scenery and diverse activities. Enjoy skiing in the winter or exploring the natural beauty that surrounds this charming town throughout the year.

Windham Mountain Resort: Experience thrilling winter sports at Windham Mountain Resort, where you can ski, snowboard, or enjoy outdoor adventures amidst stunning mountain scenery. This resort offers a vibrant atmosphere perfect for both adrenaline seekers and relaxation.
Kaaterskill Falls: Just 12 miles from Windham, Kaaterskill Falls boasts breathtaking views and a romantic ambiance. Hike the scenic trails leading to the cascading waters, making it an ideal spot for outdoor enthusiasts and nature lovers alike.
Mountain Top Arboretum: Located 8 miles away, the Mountain Top Arboretum is a family-friendly destination where you can explore diverse plant collections and enjoy peaceful outdoor settings. It’s a great place for picnics and leisurely walks.

Best time to go to Windham

The best time to visit Windham can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Windham falls in July, when visitor numbers are average and weather is mostly sunny with light rain. The coolest average temperature in Windham falls in January, visitor numbers are slightly high and weather is mostly cloudy with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	22.1°F (-5.5°C)	Light Rain	Mostly Cloudy	Slightly High	Average
February	24.1°F (-4.4°C)	Light Rain	Mostly Cloudy	Slightly High	Average
March	31.6°F (-0.2°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
April	43.3°F (6.3°C)	Light Rain	Mostly Cloudy	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 Cloudy	Slightly High	Average

Tips to save on your trip to Windham

Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
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.

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

What is the best time to go to Windham?

The best time for a Windham vacation package, especially for skiing, is typically December through March. These months offer prime conditions for winter sports at the local resorts. This is also the most popular time to visit, so you can expect a lively atmosphere and potentially higher prices for accommodations and activities.

How can I save money on a Windham vacation package?

When you bundle, you can save up to 30%*. To save money on a Windham package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

What's included in a Windham vacation package?

A Windham vacation package typically bundles round-trip flights, your hotel stay, and a rental car. Many hotels in the area offer convenient airport shuttle services, especially useful if flying into Hartford, CT (BDL-Bradley Intl.). Additionally, several hotels include free breakfast, providing a great start to your day before hitting the slopes or exploring the Catskill Mountains.Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.

What's the best vacation package for Windham?

For families, a Windham vacation package built around a stay at The Winwood Condominiums (rated 9.3 out of 10) is a strong choice. Located about 8 miles from Hunter Mountain, this property offers family rooms, a kitchen, kitchenette, game room, and an outdoor pool, with travelers frequently praising its spacious rooms and beautiful facilities, noting the overall perfect experience.Couples seeking a cozy retreat might prefer a package with Albergo Allegria Hotel, a 3.5-star property rated 9.4 out of 10. Situated about 7 miles from Hunter Mountain, it includes free breakfast, and travelers consistently highlight the top-notch breakfast and cozy overall atmosphere.If you're looking for the best value, consider a Windham vacation package with Antique Rose Inn Windham. Rated 8.4 out of 10 and costing around $150 per night, this inn is about 6 miles from Hunter Mountain and includes free breakfast, with travelers often mentioning the clean rooms and good breakfast.*Package availability and prices may change depending on dates and demand.

Is Windham a good choice for a family vacation package?

Windham is a strong choice for family vacation packages, especially for those seeking outdoor adventures and a comfortable stay. Many hotels cater to families with amenities designed for all ages.For instance, The Winwood Condominiums, rated 9.3 out of 10, offers family rooms, a game room, kitchenettes, and an outdoor pool, with travelers frequently praising the spacious rooms and beautiful facilities. Another great option is the 3.5-star Wylder Hotel Windham, rated 8.2 out of 10, which provides family rooms, an outdoor pool, and a restaurant, with travelers frequently praising the helpful staff and great facilities.Families can enjoy skiing and snowboarding at Windham Mountain Resort, located about 1 mile from central Windham. For broader outdoor exploration, Minnewaska State Park, about 17 miles from central Windham, offers hiking and scenic beauty.

What's included in a Windham ski vacation package?

Windham ski vacation packages typically bundle flights with lodging near the area's ski resorts. These packages offer a convenient way to plan your trip to this popular ski destination. For example, a Windham vacation package might include a stay at Albergo Allegria Hotel, a 3.5-star property rated 9.4 out of 10, located about 7 miles from Hunter Mountain, where travelers often praise the top-notch breakfast. Another option is Eastwind Windham, also a 3.5-star hotel rated 8 out of 10 and about 7 miles from Hunter Mountain, noted by travelers for its excellent food and accommodating staff. Lift tickets, equipment rentals, and lessons are usually separate unless specifically listed in your chosen package details.

Which Windham vacation packages include a mountain view?

Many Windham vacation packages include hotels that offer mountain-view rooms, with nearly all package hotels providing this option. When building your Windham vacation package, you can look for properties like Wylder Hotel Windham, a 3.5-star hotel rated 8.2 out of 10 by travelers, which is about 7 miles from Hunter Mountain and praised for its great facilities and amazing pool. Another excellent choice is The Winwood Condominiums, rated 9.3 out of 10 by travelers and located about 8 miles from Hunter Mountain, often highlighted for its perfect overall experience and beautiful facilities. Keep in mind that specific mountain views depend on the room type and rate you book.

What are the top things to do in Windham?

A Windham vacation centers around outdoor activities, especially skiing, with several natural attractions nearby:Browse and book things to do in Windham on Expedia.

Do you need to rent a car in Windham, or is public transport enough?

For Windham vacation packages with flights, a rental car is highly recommended. As a ski destination located outside a major city, attractions and resorts are often spread out, and a car provides the most flexibility for exploring the area and reaching ski slopes or hiking trails.Windham is served by several airports, including Hartford, CT (BDL-Bradley Intl.), which is about 83 miles away, and Albany, NY (ALB-Albany Intl.). Having a car will make it easier to get to and from the airport and navigate between different points of interest during your stay.

Are Windham vacation package hotels conveniently located?

Windham vacation package hotels are generally well-located for accessing the town's amenities and nearby ski resorts. Many properties are within easy reach of central Windham, a hub for dining and local shops.For example, Albergo Allegria Hotel, rated 9.4 out of 10, is about 1 mile from central Windham, and travelers frequently praise the friendly staff and top-notch breakfast. The Winwood Condominiums, rated 9.3 out of 10, are about a 10-minute walk from central Windham, with travelers frequently praising the beautiful facilities and good value. Another option, Hotel Vienna, rated 8.8 out of 10, is also about 1 mile from central Windham and features an indoor pool, with travelers highly recommending it and noting the convenient location. These locations provide good access to both the town and the region's outdoor attractions.

Can I change or cancel my Windham vacation package if my plans change?

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Do One Key members get extra savings when booking Windham vacation packages?

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Does Expedia offer Book Now, Pay Later Windham vacation packages?

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Windham vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

How do I find last-minute vacation packages to Windham?

To find last-minute vacation packages to Windham, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

How does free cancellation work on Windham vacation packages?

Free cancellation on a Windham vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Is it cheaper to book a Windham vacation as a package or separately?

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Windham getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Why should I book my Windham vacation package with Expedia?

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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

Windham Vacations from $603

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Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

The Latest Windham vacation packages

Hotel Vienna

Wylder Hotel Windham

The Haüs Windham

Eastwind Windham

Stay near popular Windham attractions

Windham Mountain Resort

Windham Country Club

Windham Vineyards and Winery

Huntersfield State Forest

Elm Ridge Wild Forest

Ashland Park

Windham Hotel Deals

Hotel Vienna

Wylder Hotel Windham

The Winwood Condominiums

Find the Best Windham Vacation Packages

Things to do in and around Windham

Find the best attractions in and around Windham

Best time to go to Windham

Tips to save on your trip to Windham

Windham Essential Information

More vacations you might like

Frequently asked questions

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