Title: Windham Vacation Packages 2026 | Expedia.com [Windham Travel Guide](https://expedia.com/Windham.dx175529)[Hotels in Windham](https://expedia.com/Windham-Hotels.d175529.Travel-Guide-Hotels)[Vacation Rentals in Windham](https://expedia.com/Windham-Vacation-Rentals.d175529.Travel-Guide-VacationRentals)[Flights to Windham](https://expedia.com/Cheap-Flights-To-Windham.d175529.Travel-Guide-Flights)[Things to do in Windham](https://expedia.com/Things-To-Do-In-Windham.d175529.Travel-Guide-Activities)[Car Rentals in Windham](https://expedia.com/Car-Rentals-In-Windham.d175529.Car-Rental-Guide) ![](https://images.trvl-media.com/place/175529/f5c1be28-7f99-4fb2-bc66-d538ec4615f6.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Windham Vacations ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_175529) ### 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. [](https://expedia.com/Windham-Mountain-Resort-Windham.d6087209.Vacation-Attraction) #### Windham Country Club Enjoy a round of golf in Windham at Windham Country Club. Discover the mountain views in this relaxing area. [](https://expedia.com/Windham-Country-Club-Windham.d553248621552322141.Vacation-Attraction) ## Windham Hotel Deals ![Hotel Vienna](https://images.trvl-media.com/lodging/1000000/900000/893300/893228/f91cd0d7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Vienna 107 State Route 296 Windham NY Fully refundableReserve now, pay when you stay $149 nightly $161 total Mar 12 - Mar 13 Total with taxes and fees 9.4/10 Exceptional! (776 reviews) Conveniently located and recently renovated hotel with comfortable rooms. It was a great value complete with sauna, pool and great continental breakfast. Reviewed on Mar 4, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F12%2F2026&endDate=3%2F13%2F2026&selected=893228&PinnedHotelID=893228&HadPinnedHotel=true®ionId=175529) ![Eastwind Windham](https://images.trvl-media.com/lodging/92000000/91910000/91907200/91907167/0651036f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Eastwind Windham 5088 NY-23 Windham NY $209 nightly $225 total Mar 12 - Mar 13 Total with taxes and fees 9.2/10 Wonderful! (92 reviews) Great ty, sauna was not working unfortunately Reviewed on Feb 24, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F12%2F2026&endDate=3%2F13%2F2026&selected=91907167&PinnedHotelID=91907167&HadPinnedHotel=true®ionId=175529) ![Wylder Hotel Windham](https://images.trvl-media.com/lodging/103000000/102240000/102239500/102239431/6a98f43b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Wylder Hotel Windham 19 New York 296 Windham NY $204 nightly $220 total Mar 12 - Mar 13 Total with taxes and fees 8.6/10 Excellent! (93 reviews) it's sprawling and has a lot of amenities. I think it's fabulous for kids - they had a magic show, cookie decorating, smores. They have an onsite bakery and restaurant. Tubing. They have shuttles, so you don't feel "stuck." It is very family friendly. I would say it's actually for families versus ... Reviewed on Feb 22, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F12%2F2026&endDate=3%2F13%2F2026&selected=102239431&PinnedHotelID=102239431&HadPinnedHotel=true®ionId=175529) [See all 2,101 properties in Windham](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F12%2F2026&endDate=3%2F13%2F2026®ionId=175529) 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](https://www.expedia.com/Woodstock-Music-Shop-Woodstock.d553248621532664650.Vacation-Attraction), 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](https://www.expedia.com/Hudson-Valley-Mall-Kingston.d6218019.Vacation-Attraction), 27 miles away, offering a variety of shopping and entertainment options. **Recreation** Enjoy a round of golf at [Windham Country Club](https://www.expedia.com/Windham-Country-Club-Windham.d553248621552322141.Vacation-Attraction), where you can embrace the outdoor vibes and beautiful scenery. For a nearby option, [Thunderhart Golf Course](https://www.expedia.com/Thunderhart-Golf-Course-Freehold.d553248621552322096.Vacation-Attraction) offers a similar experience just 13 miles away. For ultimate relaxation, visit [Copperhood Retreat & Spa](https://www.expedia.com/Copperhood-Retreat-Spa-Phoenicia.d553248621532664738.Vacation-Attraction), located 15 miles from Windham, for rejuvenating body treatments. **Adventure** Experience thrilling skiing at [Windham Mountain Resort](https://www.expedia.com/Windham-Mountain-Resort-Windham.d6087209.Vacation-Attraction), where adventure meets the slopes. For water fun, visit [Zoom Flume](https://www.expedia.com/Zoom-Flume-Cornwallville.d6218025.Vacation-Attraction), a family-friendly waterpark located 7 miles away. Don’t miss the [Zephyr Express Ski Lift](https://www.expedia.com/Zephyr-Express-Ski-Lift-Hunter.d553248621552112864.Vacation-Attraction), 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: ](https://www.expedia.com/Windham-Mountain-Resort-Windham.d6087209.Vacation-Attraction)** 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: ](https://www.expedia.com/Kaaterskill-Falls-Haines-Falls.d553248621532665192.Vacation-Attraction)** 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: ](https://www.expedia.com/Mountain-Top-Arboretum-Tannersville.d553248621558012064.Vacation-Attraction)** 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](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)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](https://www.expedia.com/Hunter-Mountain-Hunter.d6087205.Vacation-Attraction), [Zoom Flume](https://www.expedia.com/Zoom-Flume-East-Durham.d6218025.Vacation-Attraction) and [Blackhead Mountain Country Club](https://www.expedia.com/Blackhead-Mountain-Country-Club-Round-Top.d553248621552322110.Vacation-Attraction) | ## More vacations you might like 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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](https://www.expedia.com/why/trip-planning): 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](https://www.expedia.com/Things-To-Do-In-Windham.d175529.Travel-Guide-Activities) with our dedicated travel guide. ### Does Expedia offer Book Now, Pay Later Windham vacation packages? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - More ways to book - [Hotels near Windham Country Club ](https://www.expedia.com/Windham-Country-Club-Hotels.0-l553248621552322141-0.Travel-Guide-Filter-Hotels) - [Hotels near Windham Mountain Resort ](https://www.expedia.com/Windham-Mountain-Resort-Hotels.0-l6087209-0.Travel-Guide-Filter-Hotels) - [Hensonville Hotels ](https://www.expedia.com/Hensonville-Hotels.d6023521.Travel-Guide-Hotels) - [Apartments in Hensonville ](https://www.expedia.com/Hensonville-Apartments.d6023521-aaApartments.Travel-Guide-Accommodation) - [B&B in Hensonville ](https://www.expedia.com/Hensonville-Bed-And-Breakfast.d6023521-aaBedAndBreakfast.Travel-Guide-Accommodation) - [3 Star Hotels in Hensonville ](https://www.expedia.com/3Star-Hensonville-Hotels.s30-0-d6023521.Travel-Guide-Filter-Hotels) - 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