Windham vacation rentals

We found 777 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Windham by choosing from 149 houses, 33 condos, and other vacation rentals. Whether you're traveling with family, friends, or just your furry companion, vacation rentals have the amenities you expect for your stay, which might include parking and a washer and dryer. You'll be able to choose a rental that has what everyone needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Windham

Showing deals for:Nov 7 - Nov 14

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Magical Home Located in Windham and Catskills

Windham, NY

13% off
Price is $360
$2,518 for 7 nights
All fees included
Magical Home Located in Windham and Catskills

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Find out more about Windham

Find out more about Windham

Why visit Windham

  1. Winter Sports Paradise: Windham is renowned for its ski resorts, offering thrilling winter sports and activities for all skill levels.
  2. Scenic Nature Preserves: Explore beautiful wooded areas and nature preserves that highlight the area's natural beauty.
  3. Family-Friendly Atmosphere: Windham boasts a welcoming environment perfect for families looking for adventure and relaxation.
  4. Windham Mountain Club: A must-visit for additional recreational activities, enhancing your outdoor experience.
  5. Diverse Accommodation Options: Choose from cozy apartments, spacious homes, and charming cottages for a perfect getaway.

Popular types of accommodation in Windham

If you're searching for the perfect getaway in Windham, you're in the right place! Our most popular vacation rentals include Houses, cozy Cabins, and modern Apartments. Whether you're looking for spacious whole homes or intimate bedroom rentals, Windham offers a variety of options to suit your needs. Explore our selection of Windham retreats and discover the ideal spot for your next vacation!

  • Houses: This is the top choice for visitors seeking spacious and comfortable accommodations, ideal for families or groups.
  • Apartments: A popular option for those wanting the convenience of home amenities in a central location.
  • Cabins: Perfect for nature enthusiasts, offering a cozy retreat in a rustic setting.
  • Cottages: These charming dwellings provide an intimate and picturesque getaway.
  • Condos: A great choice for travelers desiring modern comforts in a community atmosphere.**

Top attractions in Windham

Windham, New York, is a fantastic destination for ski and adventure enthusiasts, offering a variety of attractions such as mountains, ski resorts, and nature preserves. Visitors can enjoy cultural experiences and outdoor activities perfect for families. A must-visit is the Windham Mountain Club, which provides additional recreational opportunities. Whether you're seeking thrills or a relaxing getaway, Windham has something for everyone.

  1. Windham Mountain Resort: Experience thrilling skiing and snowboarding on pristine slopes, along with cozy lodges and vibrant après-ski activities, perfect for adventure seekers and outdoor enthusiasts.
  2. Kaaterskill Falls: Discover the breathtaking beauty of this iconic waterfall, surrounded by lush landscapes, offering romantic views and adventurous hiking trails for nature lovers.
  3. Catskill Mountains: Explore stunning scenery and diverse outdoor activities, from hiking to scenic drives, in this majestic mountain range that promises unforgettable adventures.

Things to do recommended for couples

Planning a romantic getaway in Windham? Experience the thrill of skiing at Hunter Mountain or Windham Mountain Resort, both perfect for outdoor adventures. Don't forget to visit Windham Vineyards and Winery for a charming wine tasting amidst beautiful scenery—ideal for creating lasting memories together.

Things to do recommended for families

During your family vacation in Windham, you can splash around at Zoom Flume, a fun waterpark just 7 miles away, or enjoy wellness activities at the Pine Hill Community Center, located 17 miles away. Both spots offer great experiences for families looking to bond and relax together.

Things to do recommended for groups

In Windham, groups can enjoy a round of golf at Windham Country Club or Blackhead Mountain Country Club for an engaging sports experience. For adventure and family fun, visit North-South Lake Campground, just 13 miles away, offering stunning outdoor scenery and activities.

What do I need to keep in mind when booking a vacation in Windham

When planning your trip, whether you're traveling with friends, family, pets, or seeking extended stays, be sure to prioritize your preferences in your search. Here are some helpful booking tips for Vrbo to assist you.

  • Traveling to Windham with a group: Take into account how many bedrooms you'll require, as well as additional features like a fully equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Windham with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions for a more enjoyable experience.
  • Taking your pets with you to Windham: For many families, a vacation isn't truly fulfilling without their furry companion. If you can relate, explore Vrbo listings that welcome pets. Most of these pet-friendly homes come equipped with feeding bowls and beds, ensuring that all members of your family feel comfortable and at ease.
  • Planning for a long term stay visiting Windham: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Windham

Windham, New York, offers a perfect blend of adventure and relaxation for tourists. Nestled in the beautiful Merrimack Valley, this charming town is ideal for skiing and outdoor sports. Explore the surrounding wooded acres and experience the friendly atmosphere of family-friendly neighborhoods. Whether seeking thrilling activities or a peaceful retreat, Windham and its nearby areas promise a delightful vacation filled with scenic beauty and historical charm.

  • Woodstock: Located about 20 miles from Windham, Woodstock is a vibrant town known for its artistic spirit and stunning natural landscapes. This historic area, famously associated with the 1969 music festival, offers a plethora of outdoor activities including skiing at nearby resorts and hiking along scenic trails. Visitors can explore local art galleries, charming shops, and enjoy the beautiful scenery of the surrounding mountains and lakes. Don't miss the opportunity to relax in one of the local parks, where you can soak in the peaceful atmosphere and breathtaking views.
  • Kingston: Approximately 29 miles from Windham, Kingston is a city rich in history and outdoor adventure. Nestled along the Hudson River, it boasts a vibrant waterfront and plenty of recreational opportunities. Outdoor enthusiasts will find skiing and snowboarding at nearby ski resorts, as well as access to beautiful hiking trails that wind through the area's stunning mountain landscapes. Kingston's historical district features lovely parks and local landmarks, making it a perfect blend of adventure and culture.
  • Lake Hill: Just 17 miles from Windham, Lake Hill is a quaint community that offers a serene escape with its picturesque scenery. With easy access to ski fields and resorts, this area is perfect for winter sports enthusiasts. Lake Hill is surrounded by beautiful lakes and mountains, providing ample opportunities for outdoor activities such as hiking, fishing, and even beach outings during the warmer months. This charming locale invites travelers to unwind and experience the natural beauty of the Hudson Valley.

Best time to go to Windham

If you're planning a trip to Windham, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from December to February, while off-peak times, like May to June and October tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January22.1°F (-5.5°C)Light RainMostly CloudySlightly HighSlightly High
February24.1°F (-4.4°C)Light RainMostly CloudySlightly HighSlightly High
March31.6°F (-0.2°C)Light RainMostly CloudyAverageAverage
April43.3°F (6.3°C)Light RainMostly CloudyAverageSlightly Low
May55.6°F (13.1°C)Light RainMostly SunnySlightly LowSlightly Low
June63.0°F (17.2°C)Light RainMostly SunnySlightly LowAverage
July68.7°F (20.4°C)Light RainMostly SunnyAverageAverage
August66.7°F (19.3°C)Light RainMostly SunnyAverageSlightly Low
September59.9°F (15.5°C)Light RainMostly SunnyAverageAverage
October48.9°F (9.4°C)Light RainMostly SunnySlightly LowAverage
November36.7°F (2.6°C)Light RainMostly SunnyAverageAverage
December28.8°F (-1.8°C)Light RainMostly CloudySlightly HighSlightly High

Booking with Vrbo is simple

Are you hoping to save money on your next adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that suits your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway!

Save more with One Key

When you reserve a qualifying Vrbo for your group getaway, you'll receive OneKeyCash™ on the total amount of your booking. Being the organizer has its perks! By joining our OneKey rewards program, you can unlock exclusive savings for members and earn OneKeyCash™ on eligible stays. Sign up today and begin reaping the benefits.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a convenient platform for you to plan new trips, refine your existing plans, or manage your bookings effectively. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To check out the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

The tranquil city of Windham awaits you

Enjoy the wineries and other features of Windham. This relaxing city is known for its skiing, hiking and mountain views. With a vacation rental, you get a home away from home—many rentals offer full kitchens and outdoor grills for some home cooking.

Windham—water, history, and the luck of the Irish

Take a break from the pistes and enjoy a scenic 10-mile ride through Mount Hayden State Forest to the Zoom Flume Water Park. This popular family attraction features a range of exciting slides and water features, from the daredevil Black Vortex to the relaxing Lazy River. The little ones can play safely in Pelican Pond, while teenage adrenaline junkies can race their buddies down the Grand Prix Splashway. On the return journey, take a short detour into East Durham to see the historic Woodward Road Stone Arch Bridge and visit the quirky Irish gift shop.

Fun on your doorstep in Windham

Windham Mountain drew its early customer base from New York City, whose winter-sports enthusiasts could reach the slopes in around 3 hours. The ambitious resort launched itself onto the global stage in 1997, by installing lights on several lower trails to become the first mountain in the Catskills to offer night-skiing. The trail network extends over 2 peaks and provides conditions suitable for all skill levels. Thoughtful extra touches like live music and yoga sessions complement the lively après-ski scene, often within easy walking distance of Windham vacation rentals.

Windham—not just for Christmas

Windham’s relatively high elevation in the Catskill Mountains ensures a good supply of snow typically from late November through March—peak months for Windham vacation rentals near the ski resort. The town has cleverly expanded its appeal beyond the winter-sports season with a variety of summer sporting activities such as mountain biking, which benefit from warm, sunny days and cool evenings. Consistent, moderate rainfall throughout the year keeps the parks and gardens freshly irrigated and the watercourses of Schoharie Creek and Batavia Kill flowing freely.

Exploring the natural landscape of Windham

Whether you're looking for fun outdoor activities or just want to take in the scenery, Windham is a great place to get out in nature. These are some of the area's most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • Kaaterskill Falls (12.5 mi / 20.1 km)
  • Overlook Mountain Trailhead (17.6 mi / 28.4 km)
  • Catskill Mountains (21.6 mi / 34.8 km)
  • Mountain Top Arboretum (8.4 mi / 13.5 km)
  • Belleayre Beach at Pine Hill Lake (16.8 mi / 27.1 km)
  • Mine Kill State Park (13.8 mi / 22.2 km)

Traveling to and around Windham

The nearest airport is in Hudson, NY (HCC-Columbia County), located 27.6 mi (44.4 km) from the city center.

Frequently asked questions

What is the best area to stay in Windham when booking a vacation rental?
When planning a vacation rental in Windham, New York, the area around Windham Mountain is one of the best choices. This neighborhood is particularly appealing for those looking to enjoy outdoor activities, as it provides easy access to skiing and snowboarding in the winter, as well as hiking and mountain biking in the warmer months. The vibrant atmosphere surrounding the mountain attracts many visitors, making it a lively spot for families and groups of friends alike.

Another excellent area to consider is the charming downtown Windham area, where you can find a selection of cozy cottages and rental homes. This neighborhood offers a delightful blend of local shops, restaurants, and art galleries, allowing you to immerse yourself in the community's culture. Nearby, the Windham Path is a popular attraction for those who enjoy scenic walks or bike rides, offering beautiful views of the surrounding landscape.

In terms of vacation rentals, both of these areas feature a variety of properties, with Windham Mountain boasting around 200 options that cater to different tastes and budgets. Meanwhile, downtown Windham has approximately 150 rentals, providing plenty of choices for visitors seeking a more quaint and local experience.
How much does it cost to rent a vacation home in Windham?
Prices for vacation rentals in Windham vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Windham to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Windham vacation house rentals?
You can find great discounts on house rentals in Windham on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best Windham ski resort rentals?
For the best ski resort rentals in Windham, New York, travelers should focus on the areas surrounding Windham Mountain, which is known for its excellent skiing conditions and family-friendly atmosphere. The nearby village of Windham offers a variety of vacation rentals, including cozy cabins and spacious chalets that cater to different group sizes. Many of these properties come with desirable amenities such as fireplaces, hot tubs, and fully equipped kitchens, superb for unwinding after a day on the slopes.

Additionally, the area around Main Street in Windham provides convenient access to local shops, restaurants, and ski rental services, enhancing the overall experience for visitors. Rental properties here often feature rustic decor, mountain views, and outdoor spaces for enjoying the fresh air.

For those seeking a more secluded experience, the nearby Catskill Forest Preserve offers opportunities for nature lovers, where you can find rentals that emphasize tranquility and outdoor access, often including hiking trails right outside the door. Expect amenities like spacious decks, BBQ grills, and proximity to scenic viewpoints that make for memorable stays in the heart of the Catskills. See all ski-in-/ski-out rentals in Windham.
What is the most popular type of vacation rental accomodation in Windham?
In Windham, vacation houses are the most popular type of rental accommodation, with about 128 available throughout the area. These properties are often situated in scenic locations, superb for families or groups looking to enjoy the natural beauty of the Catskills. Most vacation houses typically feature multiple bedrooms, spacious living areas, fully equipped kitchens, and outdoor spaces like decks or patios for enjoying the fresh mountain air. Additionally, there are around 33 condos that offer a more communal living experience, often with shared amenities such as pools or fitness centers. For those seeking a cozier option, there are 19 cabins and 17 chalets, both providing a rustic charm and a closer connection to the surrounding wilderness.
Are there any family house rentals in Windham?
In Windham, New York, families looking for vacation rentals will find an impressive selection, with around 161 options available throughout the area. This charming town is well-known for its outdoor activities, making it an ideal spot for family getaways. Many of the homes feature spacious living areas, full kitchens equipped for preparing family meals, and cozy dining spaces that encourage togetherness.

Travelers can also enjoy amenities like game rooms for entertainment and outdoor decks or patios great for barbecues and relaxation. The area is close to Windham Mountain, where winter sports enthusiasts can ski or snowboard, while the summer months offer hiking and biking trails in the lush surroundings.

Additionally, nearby attractions such as the Windham Theatre and local farmers' markets provide opportunities for cultural experiences and fresh produce shopping. See all family-friendly rentals in Windham.
Can I rent a vacation home with a pool or hot tub in Windham?
In Windham, there are plenty of vacation homes available for rent that feature pools and hot tubs, with around 43 options to choose from. This charming town, located in the Catskills, offers a variety of rental properties across different neighborhoods, including the scenic areas near the Windham Mountain Resort, which is popular for both winter sports and summer activities.

Travelers can expect amenities such as private pools, hot tubs, spacious outdoor decks, and fully equipped kitchens, making these homes ideal for relaxation and entertaining after a day of outdoor adventures. Find your rental in Windham with a pool or a hot tub.
Can I find long-stay vacation rentals in Windham?
A long-stay vacation rental in Windham is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Windham?
In Windham, there are numerous pet-friendly house rentals available, offering a range of options for travelers seeking to bring their furry companions along. Many of these rentals come equipped with amenities such as spacious backyards, fire pits, and modern kitchens, making them ideal for families and groups.

The area around Windham is known for its beautiful natural surroundings, with easy access to hiking trails and outdoor activities suitable for pets. Nearby Windham Mountain provides opportunities for skiing in the winter and mountain biking in the summer, while also featuring pet-friendly policies in some of their outdoor areas. See all pet-friendly rentals in Windham.
Are there any remote work vacation rentals in Windham?
In Windham, New York, there are plenty of remote work vacation rentals available, with around 210 options to choose from. This charming mountain town is ideal for those looking to balance work and leisure, surrounded by beautiful landscapes and outdoor activities. Many properties come equipped with essential remote work amenities such as high-speed Wi-Fi, dedicated desks, ergonomic chairs, and even office spaces with computer monitors.

Travelers can expect comfortable living arrangements, often featuring spacious common areas and fully equipped kitchens, making it easy to prepare meals during longer stays. The proximity to local attractions like hiking trails in the Catskill Mountains and the nearby Windham Mountain Resort adds to the appeal, allowing for outdoor adventures after the workday ends. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Windham vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Windham with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Windham?
In Windham, popular rental amenities include WiFi for staying connected, fully equipped kitchens for preparing meals, and coffee or tea makers for a quick morning pick-me-up. Many properties also feature patios, allowing guests to enjoy the fresh mountain air, and blenders for those who enjoy smoothies or frozen drinks.
When is the best time to visit Windham for a vacation rental?
January is the most popular time to visit Windham, especially for those seeking thrilling winter adventures. This month falls within the peak season, which runs from December through February, and offers an array of activities such as skiing and snowboarding at the local ski resorts. With the beautiful backdrop of the Catskill Mountains blanketed in snow, outdoor enthusiasts can fully embrace the winter wonderland.

During January, temperatures typically range from the low 20s to mid-30s Fahrenheit, creating a crisp environment great for winter sports and cozy evenings by the fireplace. The community comes alive with visitors enjoying the slopes and the festive atmosphere, making it an ideal time for those who thrive on excitement and adventure.

For travelers looking for a more budget-friendly option, consider planning your visit in October. This month presents a unique opportunity to experience the stunning fall foliage, as the vibrant colors of autumn paint the landscape.
How early should I book a Windham vacation rental?
Book your Windham vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Windham?
In Windham, visitors can enjoy a variety of attractions that cater to outdoor enthusiasts and those looking for a charming mountain getaway. The Windham Mountain Resort is a major draw, offering skiing and snowboarding in the winter, as well as mountain biking and hiking trails during the warmer months. The surrounding Catskill Forest Preserve provides numerous trails for hiking, with scenic views and opportunities for wildlife observation.

The picturesque town center features quaint shops, local eateries, and seasonal festivals that celebrate the community's culture and crafts. Additionally, the nearby Kaaterskill Falls, a stunning two-tiered waterfall, is a popular spot for hiking and photography, drawing visitors to its natural beauty.
Can I change or cancel my Windham home rental booking on Vrbo?
To find Windham vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Windham vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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