Windham vacation rentals

We found 780 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Windham by choosing from 147 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
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more
  • More for less

    More space, more privacy, more amenities — more value

Find out more about Windham

Find out more about Windham

Why visit Windham

  1. Outdoor Adventures: Enjoy excellent skiing in winter and serene hiking trails in summer, perfect for adventure seekers.
  2. Stunning Scenery: Breathtaking mountain vistas and picturesque waterfalls create a stunning backdrop for your vacation.
  3. Charming Small Towns: Explore nearby towns with friendly locals, adding to the relaxing and romantic atmosphere.
  4. Family-Friendly Activities: Discover a variety of attractions suitable for all ages, ensuring fun for families.
  5. Cozy Accommodations: Choose from private homes, charming cabins, and cozy cottages for a comfortable stay.

Popular types of accommodation in Windham

Planning a getaway to Windham? You're in for a treat! Explore a variety of vacation rentals, including private homes, charming cabins, and cozy cottages. Whether you're searching for the best Windham vacation rentals or spacious house rentals, you'll find plenty of options to suit your needs. Enjoy your stay with transparency, savings, and reassurance, ensuring your trip to Windham is unforgettable!

  • Houses: The top choice for visitors, offering a spacious and comfortable stay ideal for families or groups.
  • Cabins: A charming alternative, perfect for those seeking a rustic experience surrounded by nature.
  • Cottages: Quaint and cozy, these rentals provide a delightful escape for couples or small families.
  • Chalets: A popular option, especially for those looking to enjoy the mountain scenery and outdoor activities.
  • Apartments: A practical choice for individuals or couples, offering convenience and easy access to local amenities.**

Top attractions in Windham

Windham, New York, is an ideal destination for ski enthusiasts and adventure seekers alike. With attractions such as national parks, breathtaking waterfalls, and modern civic buildings, the area offers a rich blend of outdoor activities, cultural experiences, and stunning scenery. Whether you're travelling solo, with family, or as a couple, Windham promises a memorable vacation filled with exploration and enjoyment.

  1. Kaaterskill Falls: A breathtaking two-tiered waterfall, Kaaterskill Falls offers a romantic and adventurous atmosphere. The scenic hike to the falls features stunning views of the surrounding wilderness, making it a perfect spot for nature lovers and photographers.
  2. Mountain Top Arboretum: This beautiful arboretum is a wonderful destination for families, featuring a diverse collection of trees and plants. Enjoy leisurely walks along well-maintained trails while immersing yourself in the serene natural environment.
  3. Catskill State Park: A vast natural playground, Catskill State Park offers numerous outdoor activities such as hiking, fishing, and camping. Its breathtaking landscapes and rich wildlife provide an excellent backdrop for adventure seekers and nature enthusiasts.

Things to do recommended for couples

Windham, New York, offers a perfect romantic getaway. Enjoy skiing at Windham Mountain Resort, explore the serene beauty of Windham Vineyards and Winery, or take an adventurous ride on the Northern Express Ski Lift, just 11.3km away. Embrace the charm and create unforgettable memories together!

Things to do recommended for families

Families visiting Windham can have a splashing good time at Zoom Flume, a waterpark located 11.3km away. With its exciting water slides and family-friendly attractions, it promises a day full of adventure and entertainment for all ages.

Things to do recommended for groups

Enjoy a round of golf at the Windham Country Club or venture to the Blackhead Mountain Country Club for more outdoor fun. Don’t miss the Woodstock Music Shop, just 32.2km away, where you can explore unique musical treasures with your group.

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

When planning your trip—whether you're traveling with a group, family, pets, or seeking extended stays—it's important to prioritize your preferences effectively. Here are some helpful tips for booking on Vrbo.

  • Traveling to Windham with a group: Think about how many bedrooms you require, along with amenities like a full kitchen or outdoor space for gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Windham with young kids: Travelling with young children can present its challenges. It's important to prioritize their comfort and safety, along with ensuring access to suitable amenities, like a private swimming pool. Additionally, considering your closeness to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Windham: For many families, a trip isn’t truly complete without their furry companions. If that resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Windham: If you're seeking vacation rentals with special offers 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 rentals. Don't forget to include options like a parking spot, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Windham

Windham, New York, is a hidden gem perfect for adventure seekers and families alike. With its stunning mountain vistas, it offers excellent ski options in winter and serene hiking trails in summer. Nearby, you'll find charming towns with friendly locals, creating a relaxing and romantic atmosphere. Don't miss the beach access for a refreshing escape and explore family-friendly vacation spots that make Windham an ideal getaway for all ages.

  • Hunter: Located 11.3km away from Windham, Hunter is renowned for its stunning mountain landscapes and outdoor adventures. A popular destination for skiing enthusiasts, it boasts excellent ski fields and resorts that cater to all skill levels. In addition to winter sports, visitors can explore the area's picturesque lakes and waterfalls, making it a year-round playground for adventure seekers. Whether you're hitting the slopes or hiking along scenic trails, Hunter offers an exhilarating travel experience.
  • Tannersville: Situated 16.1km from Windham, Tannersville is another gem for outdoor aficionados. This charming town combines a laid-back atmosphere with thrilling activities, particularly in the winter months when skiing takes centre stage. With access to ski resorts and stunning natural surroundings, Tannersville is perfect for those looking to immerse themselves in nature. The nearby mountains, lakes, and waterfalls provide a backdrop for exploration and relaxation, ensuring a memorable visit.
  • Hensonville: Just 3.2km from Windham, Hensonville offers a quaint escape with a focus on outdoor sports and adventure. This small city is ideal for those seeking a more intimate experience while enjoying the same thrilling activities available in the nearby areas. With ski resorts and beautiful natural landmarks like mountains, lakes, and waterfalls within easy reach, Hensonville serves as a perfect base for exploring the region while enjoying the excitement of winter sports.

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 CloudyAverageSlightly Low
April43.3°F (6.3°C)Light RainMostly CloudyAverageSlightly Low
May55.6°F (13.1°C)Light RainMostly SunnySlightly LowAverage
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 SunnyAverageSlightly Low
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 on your upcoming journey? Being flexible with your travel dates can make a significant difference, as prices tend to vary. Additionally, opting for a longer stay often leads to considerable savings. To discover the perfect Vrbo property that fits your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you make the most of your travel experience!

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for you to plan new adventures, manage your existing itineraries, or review and organise your reservations. Your saved or booked properties are neatly categorised into Potential, Upcoming, or Current Trips. To discover Trip Boards, please visit: https://www.vrbo.com/en-ca/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.

Activities and attractions in Windham

Do you want to find top things to see and do in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that Windham has to offer. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Hunter Mountain (7.4 mi / 12 km)
  • Windham Country Club (1 mi / 1.6 km)
  • Windham Mountain Resort (1.2 mi / 1.9 km)
  • Windham Vineyards and Winery (3.4 mi / 5.4 km)
  • Zoom Flume (7.4 mi / 11.9 km)
  • Kaaterskill Falls (12.5 mi / 20.1 km)

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:

  • Catskill Mountains (21.6 mi / 34.8 km)
  • Mountain Top Arboretum (8.4 mi / 13.5 km)
  • Kaaterskill Falls (12.5 mi / 20.1 km)
  • Belleayre Beach at Pine Hill Lake (16.8 mi / 27.1 km)
  • Overlook Mountain Trailhead (17.6 mi / 28.4 km)
  • East Branch Delaware River (23 mi / 37.1 km)

Seasonal weather in Windham

Travelers enjoy Windham for its skiing. To make the most of the cold weather activities, you might consider visiting in January, March, December or November, when snowfall averages 7 inches and temperatures average 27°F.

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 most popular type of vacation rental accommodation in Windham?
The most sought-after types of vacation rentals in Windham are houses. Hoping for something different? Vrbo has plenty of options to match our guests' diverse needs, so you'll see vacation properties in all sizes, and for all budgets. The ideal fit is waiting for you — find yours today.
How much does it cost to rent a vacation rental in Windham?
Season, property type and length of stay are some factors that can affect the price of a vacation home. Simply add your dates of travel to find the ultimate escape. From comfy cottages to sprawling villas, all Vrbo vacation rentals provide incredible value.
How much does it cost to rent a beach house in Windham?
Prices for beach houses in Windham may vary depending on the type and size of the property and when you're traveling. All you have to do is enter your travel dates into Vrbo and the number of guests to view vacation rental options and prices. From there you can use our filters to narrow your search by nearby activities, amenities, ratings and more.
Are there pet-friendly vacation rentals in Windham?
With 34 vacation rentals that allow pets, your furry friend can join in the fun on your Windham break. Use the filter tool to search our pet-friendly vacation rentals and find a stay that's pawfect on Vrbo.
Can I rent a house with a pool in Windham?
Tick the "pool" box in our filter tool and you can choose from 20 houses with private pools in Windham on Vrbo. Morning swim, afternoon splash or midnight soak? How you spend your free time is up to you when your vacation property boasts its own swimming pool.
What are popular rental amenities in Windham?
A sauna, a barbecue grill and a lake view rank as the most popular rental amenities in Windham. Whether you plan to travel as a party of one, with your other half or a bunch of friends, Vrbo will help you find a vacation rental that matches your tastes with all the features you need.
Are there large group vacation rentals in Windham?
Windham has 17 vacation rentals that can cater to 10 or more people. These properties come with plenty of space to enjoy good times with your nearest and dearest.
Are there vacation rentals in Windham that welcome kids?
Windham has 34 family-friendly vacation rentals. And finding a stay that welcomes kids is easy with Vrbo's "Properties good for families" filter. In addition to having the whole place to yourselves, you'll get access to perks and conveniences like extra bedrooms, pools and kitchens.
What are the top attractions for families in Windham?
Keeping the kids happy during your vacation in Windham is a breeze with these family-friendly attractions:

  • Zoom Flume
  • Mountain Top Arboretum
  • Hunter Mountain

Can I find two-bedroom vacation rentals in Windham?
Take off with your besties and enjoy total privacy and comfort in one of the eight two-bedroom vacation rentals Windham has to offer.
Are there vacation rentals with WiFi in Windham?
Whether you want to keep up with the headlines, send some emails or post a pic to social media, there are 15 vacation homes with WiFi in Windham. Check the "WiFi" box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in Windham?
Windham has 16 vacation rentals where you can kick back in air-conditioned comfort. To find a stay on Vrbo with this amenity, enter your dates of travel and use the filters to select the "air conditioning" box.
How old do you have to be to rent a vacation rental in Windham?
We advise checking with the Windham vacation property you want on Vrbo as the minimum age differs. However, it's generally 16, 18 or 21.
How long can I rent a vacation rental in Windham for?
It all depends on the Windham property. To view a list of options offering extended stays, just enter your travel dates and number of people into Vrbo's search page. Look forward to having the whole place to yourself, as well as amenities such as a full kitchen, air conditioning and outdoor spaces to play in. Be on the lookout for long-term stays that offer discounted weekly or monthly prices.
Vacation Rental options in Windham

More Vacation Rentals ideas

People also search for