Discover a selection of 500 vacation rentals in Windham, NY that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $80 per night, and houses and cabins are popular options for a stay in Windham. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Windham
Destination guide

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.

Things to do

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.

Natural features

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)
  • Belleayre Beach at Pine Hill Lake (16.8 mi / 27.1 km)
  • Esopus Creek (28.1 mi / 45.3 km)
  • Mountain Top Arboretum (8.4 mi / 13.5 km)
How to get there

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.

What are the top vacation rentals in or near Windham?

Whatever your vacation needs, you'll find a rental property in or around Windham that fits you like a glove. Why not try these on for size?:

  • "Luxury Waterfront Escape Perfect For Families And Corporate Retreats" is a favorite with guests. Around 25 miles from Windham, it has 6 bedrooms and lots of amenities to help you feel at home, including a kitchen island and nearby hunting activities.
  • Alternatively, get comfortable at "Charming Mountain Retreat Lg Mod". Located around 2 miles from the heart of Windham, it has 3 bedrooms and features a washing machine and a wood stove.

For even more great options, use the search bar at the top of the page to find the perfect Windham vacation rental for you.

Can I find log cabins to rent in or near Windham?

Often found in pristine natural spaces, log cabins offer a cozy retreat from the worries of everyday life. If you're ready to switch off for a while, check out these log cabins to rent in Windham:

  • Settle in at "Dream Log Cabin 110 Acres/hot Tub" in Rhodes Old Town and during the day enjoy snowmobiling and water skiing and your nights relaxing in comfort in your cozy cabin.
  • Alternatively, check out "Luxury Log Cabin With Amazing Views Of Windham Mountain". Try some snowboarding or skiing or just rest and relax at this Windham retreat.

What are the top-rated vacation rentals for weekend getaways in or near Windham?

Get far away from the treadmill of daily life at one of our weekend getaways in or near Windham. Whether you want to catch up with friends or spend time with the family, we'll have something to suit your style. Try these top-rated properties on for size:

  • Get comfy at "Carriage House 110 Acres In Catskills Golf Hike Swing Set Bbq". About 14 miles to the east of Windham, it has all you need for a chilled out stay, including spa and beauty services and a living room.
  • "Hunter Mountain Condo 2 Minutes From Ski Area" is another excellent option to consider. It's located about 9 miles to the southeast of Windham and features nearby birdwatching activities, internet services and more.

Can I find studio apartments for rent in and around Windham?

Studio apartments are a simple yet stylish option, ideally suited for couples or solo adventurers. Spend your days exploring your new surroundings and your nights relaxing in your cozy hideaway. The following options in or near Windham are guaranteed to please:

  • After an exciting day of urban exploration, relax in total comfort at "Tentrr Signature Site - Pleasant Valley Maplecroft Camp". A balcony and off-street parking options are just two of the amenities on offer here.
  • "Catskill Getaway - Great For Skiers. 2 Miles To Windham Mountain" is another superb stay, providing all you need for a great Windham retreat. Useful amenities here include nearby hunting activities and air conditioning.

Can I find short term rentals in or near Windham?

Whether you're after a compact apartment or a house big enough to fit the family, you'll find the perfect place on Vrbo. Squeeze in a quick break at one of these favorite picks in or near Windham:

  • For an awesome weekend away, it's hard to go past "7bdr/5bth, Amazing View, Lake, 1". It's near the center of Windham, along with lots of things to put on your itinerary.
  • Another excellent option is "5 Star Lakefront Lodge, 4 Acre Peninsula. Wifi". Round up a few friends and enjoy a comfy stay near the heart of Windham.

What are the best romantic weekend getaways in or near Windham?

Whether spent in a cabin, a cottage or a houseboat, a romantic weekend getaway is an excellent way to add some fire to your relationship. Whisk your partner away for a few days at one of these enticing escapes in or near Windham:

  • Around 25 miles from Windham, "Luxury Waterfront Escape Perfect For Families And Corporate Retreats" is the ideal place for starry-eyed couples. Beauty services and winery tours are some of the many amenities here.
  • "Charming Mountain Retreat Lg Mod" is another option that'll impress. It's approximately 2 miles from Windham and comes with winery tours and a fireplace.

Are there large vacation rentals that sleep 30 or more in or near Windham?

Whether you're organizing a birthday party, a wedding or an unforgettable vacation with a bunch of your besties, we'll help you find the perfect space to fit your group. Bring together the gang and browse these large vacation rentals in or near Windham:

  • "Windham Manor' On 45 Acres - 5 Mi. To Ski Resort": With 12 bedrooms sleeping up to 33 people, there's plenty of space for everybody. You and your guests will have access to a multitude of amenities including a fireplace and a kitchen.
  • "A'neils West Windham House": Get your whole gang's tick of approval at this retreat which comes with a kitchen and mountain views. With 10 bedrooms, up to 30 of your loved ones can stay and play here.

What are the best houses for rent with a pool in or near Windham?

A pool is often an all-important amenity when choosing where to stay on vacation, particularly if you're traveling with kids who are full of beans. Browse these houses with a pool in or near Windham and spend your days splish-splashing around:

  • Treat the gang to a memorable stay at "Carriage House 110 Acres In Catskills Golf Hike Swing Set Bbq". There's a lot to love about this retreat besides its pool, such as a dining table and a kitchen.
  • Spend leisurely days splashing around or enjoying peaceful moments by the water at "Guest House Catskill Mountains Private Backyard Fire Pit Deck 150". This vacation rental is another guest favorite and offers a separate dining area, nearby birdwatching activities and more.

Don't know how to pack your suitcase for your Windham getaway? This leading destination has a humid continental climate. During the summer months, expect average temperatures of between 55 ºF and 75 ºF. Browse our range of Windham vacation rentals by using the search bar at the top of the page. Simply adjust the filters to get more great ideas about where to stay.

What are the best large family vacation rentals in or near Windham?

Whether your ideal escape is high in the hills or on the beach, you'll have a lot more fun if you share it with your favorite people. Book one of these large family vacation rentals in or near Windham and bring along the whole gang:

  • Sleeping up to 27 guests in 6 bedrooms, "Luxury Waterfront Escape Perfect For Families And Corporate Retreats" is the perfect place to vacation with the family. This top-rated retreat is 25 miles to the east of Windham and has amenities such as a garden and a smart TV.
  • "7bdr/5bth, Amazing View, Lake, 1" also has the space you need to live it up with loved ones. This property is around 8 miles to the south of central Windham and accommodates as many as 20 guests in its 7 bedrooms. Snowsport activities and a DVD player will help keep everyone comfortable and happy.

When you want to step outside your front door, there are lots of family-friendly attractions nearby to keep everyone entertained. Kaaterskill Falls, Zoom Flume and Bailiwick Ranch and Discovery Zoo should be on your to-do list.

Can I find family cabin rentals in or near Windham?

Vacation with your kiddos in a family cabin rental in or near Windham and create some incredible new memories together. Check out these favorites:

  • "Dream Log Cabin 110 Acres/hot Tub" - This popular retreat offers childrens activities and a barbecue grill and is located approximately 3 miles to the southwest of central Windham.
  • "Cabin - Windham Mountain Ski Retreat - Hot Tub" - This stay is another top pick with families and is around 2 miles east of Windham. Offering a barbecue grill, a garden and more, it'll get everyone's nod of approval.

For more options, use the search bar at the top of the page and adjust the filters to find the Windham vacation rental that's perfect for your needs.