Windham vacation rentals

We found 801 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Windham by choosing from 150 houses, 32 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:May 29 - Jun 5

Image gallery for Slopes 5 mins away! Conditions are still great! Come enjoy! Hot tub and more!

Tannersville Farmhouse in the summer!
10 out of 10, Exceptional, (87 reviews)
Exceptional
(87 reviews)

Slopes 5 mins away! Conditions are still great! Come enjoy! Hot tub and more!

Tannersville

13% off
Price is $1,261
$8,825 for 7 nights
All fees included
Slopes 5 mins away! Conditions are still great! Come enjoy! Hot tub and more!

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Find out more about Windham

Why visit Windham

  • Winter Sports Paradise: Windham is renowned for its picturesque ski resorts, making it a top destination for skiing and snowboarding.
  • Breathtaking Waterfalls: Discover stunning waterfalls that enhance the area's natural beauty and provide excellent photo opportunities.
  • Outdoor Activities: Enjoy hiking, biking, and exploring nearby state parks for year-round adventure.
  • Charming Accommodations: Choose from cozy cabins, private homes, and charming cottages for a comfortable stay.
  • Friendly Community: Experience the warm hospitality of locals in a relaxing atmosphere that adds to the vacation vibe.

Popular types of accommodation in Windham

If you're exploring vacation rentals in Windham, you're in for a treat. The area boasts a variety of popular accommodations, including houses, cozy cabins, and charming cottages. Whether you're looking for condo rentals in Windham or house rentals for a family getaway, we've got the perfect options to suit your needs. Enjoy the beauty of Windham with the reassurance of finding the ideal place to stay.

  • Houses: The top choice among travelers visiting Windham, these homes offer spacious and comfortable accommodations, perfect for families and groups.
  • Cabins: A favorite for those seeking a rustic getaway, cabins provide a cozy retreat surrounded by nature.
  • Cottages: These charming and quaint spaces are ideal for a romantic or intimate escape.
  • Apartments: Conveniently located, apartments offer a home-like feel with modern amenities for a relaxed stay.
  • Chalets: Perfect for ski enthusiasts, chalets combine comfort with stunning mountain views.**

Top attractions in and around Windham

Windham, New York, is an ideal destination for ski enthusiasts and adventure seekers alike. With its picturesque ski resorts, stunning waterfalls, and nearby state parks, there's no shortage of outdoor activities and scenic experiences. Whether you're looking to hit the slopes or explore the rich culture and natural beauty, Windham offers a variety of attractions that cater to all types of travelers.

  • Windham Mountain Resort: A premier ski resort offering thrilling winter sports and year-round outdoor activities. Enjoy stunning mountain views, pristine slopes, and a vibrant atmosphere perfect for adventure seekers and families alike.
  • Kaaterskill Falls: A breathtaking waterfall located 12 miles from Windham, renowned for its cascading beauty. The scenic hiking trails lead to stunning viewpoints, making it a romantic and adventurous spot for nature lovers.
  • Mountain Top Arboretum: Situated 8 miles from Windham, this arboretum features diverse plant collections and peaceful walking trails, ideal for family outings and a relaxing day in nature.

Things to do recommended for couples

Ready for a romantic getaway in Windham? Start your adventure at Windham Mountain Resort for skiing and outdoor fun, then savor a delightful wine tasting at Windham Vineyards and Winery. For an unforgettable view, take a ride on the Zephyr Express Ski Lift just 7 miles away.

Things to do recommended for families

Families visiting Windham can have a splashing good time at Zoom Flume, a thrilling waterpark located 7 miles away. With exciting water slides and family-friendly attractions, it's perfect for a day filled with adventure and fun.

Things to do recommended for groups

Groups visiting Windham can enjoy a round of golf at the Windham Country Club or the nearby Blackhead Mountain Country Club, both offering a fantastic outdoor atmosphere. Don’t miss the chance to explore the Woodstock Music Shop for unique finds just a short drive away.

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

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

If you're traveling with a group, as a family, bringing your pets, or seeking extended stays, be sure to use the appropriate filters to match your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Windham with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to Windham with young kids: Traveling with little ones can present some challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Windham: For many, a family vacation wouldn’t feel whole without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly accommodations offer feeding bowls and cozy beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Windham: If you're in search of vacation rentals that offer discounts for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Windham

Windham, New York, is a hidden gem perfect for ski enthusiasts and adventure seekers. Nestled in the Catskills, it offers a relaxing atmosphere with friendly locals and stunning scenery. Nearby neighborhoods provide family-friendly vibes and secluded spots for unwinding. Explore nearby areas for more outdoor activities and charming towns, making Windham an ideal vacation destination for those looking to blend adventure with tranquility.

  • Hunter: Nestled approximately 7 miles from Windham, Hunter is a vibrant city renowned for its exhilarating ski experiences and outdoor adventures. The area is a haven for sports enthusiasts, offering access to a variety of ski fields and resorts. In addition to skiing, visitors can explore the stunning local landscape, featuring majestic mountains, serene lakes, and breathtaking waterfalls. Whether you’re hitting the slopes or enjoying leisurely hikes, Hunter provides a perfect blend of adventure and natural beauty.
  • Hensonville: Located just 2 miles away from Windham, Hensonville is a charming city that attracts thrill-seekers and outdoor lovers alike. With its close proximity to popular ski resorts and fields, it serves as a fantastic base for winter sports activities. Beyond skiing, the surrounding area is dotted with picturesque mountains, tranquil lakes, and scenic waterfalls, making it ideal for hiking and exploration. Hensonville's welcoming atmosphere and outdoor offerings ensure a memorable experience for all visitors.
  • East Windham: Situated within the Windham area, East Windham is a delightful village perfect for those seeking adventure and outdoor activities. Visitors can enjoy easy access to ski resorts and fields, making it a popular spot for skiing enthusiasts. The village is also close to beautiful mountains, an exciting theme park, and a national state park, providing ample opportunities for exploration and recreation. Whether you’re looking to hit the slopes or enjoy nature, East Windham offers a diverse range of experiences for every traveler.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 CloudyAverageSlightly Low
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 SunnyAverageAverage
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

Planning your next getaway and hoping to save some money? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking a longer stay to take advantage of some great savings. To find a Vrbo property that suits your budget, simply use our filters to narrow down options by price, location, and type of vacation rental. We're here to help you make the most of your travel experience.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash with your booking. Being the planner has its rewards. When you join our travel rewards program, OneKey, you can immediately access member discounts and earn or use OneKeyCash on eligible reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning made easy

Vrbo's user-friendly Trip Board offers you a dedicated area to plan new adventures, pick up right where you left off, and manage your travel arrangements with ease. You can easily access the properties you've saved and booked, now categorized under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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, New York, United States of America when booking a vacation rental?
When considering a vacation rental in Windham, New York, the area around the village center is an excellent choice. This neighborhood offers a charming small-town atmosphere, making it easy to explore local shops, cafes, and restaurants. A key attraction in this area is the Windham Mountain Resort, which is fantastic for skiing in the winter and mountain biking during the warmer months. Additionally, you can enjoy the beautiful scenery and hiking trails at nearby Kaaterskill Wild Forest, great for outdoor enthusiasts looking for adventure.

Another appealing area is the surrounding countryside, where you can find more secluded properties with stunning views of the Catskill Mountains. This region is ideal for those seeking tranquility and a connection with nature, with convenient access to hiking trails and picturesque landscapes.
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 near Windham, travelers should consider the areas surrounding Windham Mountain, which is known for its excellent skiing conditions. The village of Windham itself offers a variety of accommodation options, from cozy cabins to modern condos, many of which come equipped with amenities like fireplaces, ski storage, and fully equipped kitchens for post-ski meals.

In addition to Windham, nearby towns such as Hensonville and Maplecrest also feature charming rental properties, often with rustic designs that capture the essence of the Catskills. Many of these rentals provide amenities such as outdoor spaces for relaxing in the fresh mountain air, hot tubs for soaking after a day on the slopes, and proximity to local eateries and shops, enhancing the overall experience for visitors.

For those looking for more than just skiing, the area offers opportunities for hiking and exploring the beautiful surrounding landscape, with rentals often situated near scenic trails.
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 in the area. These spacious homes are ideal for families or groups, often featuring multiple bedrooms, fully equipped kitchens, and cozy living areas. Many also have outdoor spaces such as decks or patios, great for enjoying the beautiful mountain scenery. Additionally, there are around 32 condos, which provide a more compact option while still offering amenities like kitchenettes and access to communal facilities. Chalets, cabins, and apartments also contribute to the variety of options, with 20 chalets, 18 cabins, and 15 apartments available, suiting different preferences and group sizes.
Are there any family house rentals in Windham?
In Windham, New York, families will find a wealth of options with approximately 157 vacation rentals available. The area is known for its stunning natural beauty and outdoor activities, making it an ideal spot for family getaways. Many of these homes feature spacious living areas, fully equipped kitchens for home-cooked meals, and outdoor spaces superb for children to play and explore.

Visitors can stay near the Windham Mountain Resort, which offers year-round recreational activities such as skiing in the winter and hiking during the warmer months. Additionally, families will appreciate the close proximity to local parks and scenic trails, enhancing their outdoor experiences.
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 48 options to choose from. This picturesque town in the Catskill Mountains offers a variety of rental choices, from cozy cabins to spacious lodges. Many properties come equipped with private pools, hot tubs, and outdoor patios, great for relaxation after a day of exploring the scenic surroundings or hitting the slopes in winter. Travelers can also expect amenities such as fully equipped kitchens, spacious living areas, and often, fireplaces for added comfort.
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, travelers can find a variety of pet-friendly house rentals, with approximately 96 options available. Many of these properties are equipped with essential amenities such as fully stocked kitchens, cozy living spaces, and outdoor areas where pets can roam. The rentals often feature charming mountain decor, fireplaces, and decks that provide scenic views of the surrounding landscape.

Windham is known for its beautiful outdoor settings, making it a great destination for pet owners. Nearby, the Windham Mountain Resort offers outdoor activities year-round, from skiing and snowboarding in winter to hiking and mountain biking in the warmer months. While not exclusively pet-friendly, the trails in the area are great for walks with your furry companions, and the picturesque scenery adds to the overall experience.
Are there any remote work vacation rentals in Windham?
In Windham, New York, there are plenty of remote work vacation rentals available, with around 218 options to choose from. This charming town, located in the Catskill Mountains, offers a mix of cozy cabins, spacious homes, and modern condos that cater to remote workers. Many properties are equipped with high-speed internet and Wi-Fi, ensuring a reliable connection for those needing to work from home. Travelers can expect comfortable workspaces, often with scenic views, and amenities like fully equipped kitchens for meal preparation and relaxation areas to unwind after a day of work.

Additionally, Windham's proximity to outdoor activities, such as hiking, skiing, and exploring local attractions, provides a great balance of work and leisure. 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 full kitchens, allowing guests to prepare their own meals while enjoying the convenience of home. Many properties also feature cozy fireplaces, ideal for warming up after a day on the slopes. Decks or patios are common, providing outdoor space to relax and take in the beautiful mountain views. Onsite parking is typically available, making it easy for travelers to access their accommodations. Additionally, most rentals come equipped with coffee and tea makers, ensuring guests can enjoy a warm beverage at their leisure.
When is the best time to visit Windham for a vacation rental?
January is the most popular time to visit Windham, as it falls within the peak season from December to February. This winter wonderland attracts travelers eager to embrace outdoor adventures, particularly skiing and snowboarding at the renowned Windham Mountain Resort. With the slopes covered in fresh powder, visitors can enjoy exhilarating runs amid stunning mountain views.

During January, temperatures typically range from the low 20s to mid-30s Fahrenheit, creating a crisp and invigorating atmosphere superb for winter activities. The town comes alive with a cozy charm, offering plenty of opportunities for après-ski relaxation, including warm meals at local restaurants and quaint shops to explore.

For those looking for a more budget-friendly option, October presents a beautiful time to visit Windham. The fall foliage transforms the landscape into a vibrant tapestry of colors, making it ideal for scenic hikes and leisurely drives through the Catskills. This quieter month allows for a peaceful retreat, with fewer crowds and the chance to enjoy the natural beauty at a more leisurely pace.

Ultimately, the best time to book a vacation rental in Windham depends on your preferences—whether you're drawn to the bustling energy of the winter sports season or the serene beauty of autumn's colors.
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, New York, United States of America?
In Windham, New York, visitors can enjoy a variety of attractions located in the scenic Catskill Mountains. The Windham Mountain Resort is a major draw, offering skiing in the winter and mountain biking and hiking during the warmer months. Vacation rentals nearby provide easy access to the slopes and breathtaking views of the surrounding landscape.

For those looking to explore the outdoors, the nearby Catskill Forest Preserve features numerous hiking trails, including the popular hike to Kaaterskill Falls, which is a stunning waterfall that attracts many nature enthusiasts. The charming downtown area of Windham offers quaint shops, local eateries, and seasonal events, creating a vibrant community atmosphere.

Additionally, just a short drive away, the town of Hunter features more outdoor activities and attractions, including the Hunter Mountain Resort, which also offers year-round fun with zip-lining and festivals during the summer.
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 cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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