Vacation rentals in Windham

4.99 out of 5 average rating, 135 reviews

Chalet in Windham

Gorgeous Modern Lodge w/ Mt View - 5 Min to Skiing

Plan your all-seasons escape to this gorgeous new mid-century modern chalet with can't-beat direct views of Windham Mtn, less than a 5 minute drive away. Situated between state land and an active creek, enjoy this mountain getaway's hot tub, firepit, game room, open floor plan and other luxury amenities. Just 2.5 hours from NYC, and minutes away to skiing (<5 min to Windham Mtn, 15 min to Hunter Mtn, 40 min to Belleayre Mtn), hiking, biking, swimming, golfing, fishing, vineyards and restaurants!

4.99 out of 5 average rating, 366 reviews

Custom Catskills private retreat

This is a 2 bedroom 1 bath house located just 7 minutes from the Windham ski mountain. The house is surrounded by scenic land with few neighbors to be seen. Skiing, fall foliage, swimming holes, hiking, golf, antiquing, horseback riding, local farms are just a few things to name that this area has to offer. The house itself is a true retreat, you will leave totally re-charged - sweet air, bird chirping, star gazing, grilling, bong fire or simply enjoy a few days of not seeing another soul :)

4.89 out of 5 average rating, 193 reviews

A park setting is depicted, featuring manicured green grass with basketball courts in the foreground. Lush trees surround the area, and a calm body of water is visible in the background. The sky is clear, with a few fluffy clouds, adding to the serene atmosphere.

Condo in Windham

Cozy Hideaway Windham, Hunter ,Pool,Pickleball.

Spacious 1BR condo for a max. of 4 guests , sleeps 2 in separate bedroom , additional 2 on an inflatable airbed . Balcony with mountain view ,2 tennis courts ,outdoor pool . Awesome location . Windham and Hunter within reach .Get close to nature in the nearby hiking trails, Windham Path, Kaaterskill Falls. Kayaking on North-South Lake or ziplining in Hunter,skiing ,snowboarding ,golfing and mountain biking . Leave your worries at home and come to relax.Enjoy many dining options in town.

4.95 out of 5 average rating, 439 reviews

The chalet's exterior is illuminated by soft string lights at dusk, highlighting the rustic wooden structure. A cozy seating area with chairs and a hot tub is situated on the deck, framed by tall trees, creating a serene outdoor retreat.

Cabin in Windham

CozyCatskillChalet w/ Hot Tub (Catskill Mountains)

At face value, IG: @cozycatskillchalet appears to be just a humble little getaway tucked in the Catksill Mountains of Windham, NY. But even the most discerning guests will be quickly spirited away by the rustic charm and postcard-eqsue surroundings all around. At night, can't-be-beat stargazing on the back deck (or while soaking in the hot tub) will have you convinced this humble hideaway is a lot more illustrious than it lets on. Disclaimer: The chalet is not a luxury hotel or property.

4.95 out of 5 average rating, 145 reviews

Home in Hunter

Modern House with Mountain View @Getawind

Experience luxury and comfort in our newly built property. Marvel at the breathtaking panoramic views of Rusk mountain through floor-to-ceiling windows. Unwind in the sauna or hot tub, and gather around the fire pit for cozy evenings. Enjoy outdoor movie nights with our projector, or savor grilled delights in the patio area. Warm up by the fireplace, explore Ski resorts, Golf Clubs and more. It's the perfect retreat for families and friends. Book now and create unforgettable memories!

4.99 out of 5 average rating, 160 reviews

Guesthouse in Windham

Alpine Chalet on Spectacular Property

Inspired by their travels in the Swiss Alps, the hosts of the Mountaintop Chalet invite guests to their peaceful alpine guesthouse atop a mountain in the Northern Catskills. Nestled on a quiet, private road, the Mountaintop Chalet is just an 8 minutes drive to downtown Windham, NY, 10 minutes to Windham Mountain and 18 minutes to Hunter Mountain. This tranquil yet accessible setting makes it the perfect escape for couples, families and friends. Follow on Insta at mountaintop_chalet.

4.9 out of 5 average rating, 242 reviews

A charming cabin is surrounded by tall trees, showcasing a wooden exterior with a gabled roof. Two red chairs sit invitingly on the porch, while large windows allow natural light to fill the space. A tranquil outdoor setting is emphasized by the greenery.

Cabin in Prattsville

Little Red Cabin Near Windham & Hunter w/ Hot Tub

Nestled in the woods, our 3 bedroom cabin offers the perfect escape from the hustle and bustle of everyday life. The cozy interior features a warm, inviting atmosphere with all the amenities you need for a comfortable stay. The spacious living room is the perfect place to unwind after a long day of exploring the great outdoors, complete with a cozy fireplace and outdoor hot tub that offer stunning views of the surrounding landscape. Follow us on IG @thelittleredcabinny

4.95 out of 5 average rating, 125 reviews

Cabin in Windham

The Creekside Cabin - 5 mins to Windham Mt!

Nestled in the hills of Windham NY, the Creekside Cabin is a hidden gem just under 2.5 hours from NYC. Ideal for families and small groups of friends, this cozy cabin features three bedrooms, one bathroom, a comfortable living room overlooking a tranquil creek, and a fully equipped kitchen with a wood-burning fireplace. Whether you're looking for a weekend escape or a longer retreat, the Creekside Cabin offers a peaceful and relaxing stay in a beautiful natural setting.

4.9 out of 5 average rating, 119 reviews

A wooden balcony offers a view of the grassy yard below, where two white chairs are positioned beside a tree. In the background, several townhouse structures are visible, surrounded by landscaped greenery and under a clear blue sky.

Townhouse in Windham

Windham Mountain Village 2 bedroom townhouse

This 2 bedroom, 2 bath Townhouse with loft that sleeps 8 (max 6 adults) is located at the top of Windham Mt Village a very short walking distance from the Windham ski lodge and beginner lifts. Fully equipped kitchen, dining area, living area with fireplace including firewood. TV with cable and free high speed wifi. Outdoor deck with gas grill. Washer and Dryer. 2 parking spots in front. Access to community pool and hot tub when open. Air Conditioning in summer.

Superhost

A cozy corner features three wooden stools against a textured gray wall. Next to them, a compact, folded table is positioned, accompanied by a small black side table containing a potted plant. A lamp stands on the side table, providing soft illumination.

Condo in Windham

4.73 out of 5 average rating, 280 reviews

Summer Retreat w/ Balcony & inground Pool

Leave your worries at home and come relax in our newly renovated, one bedroom condo in the heart of the Catskills. welcome to our end unit,features wood burning fireplace, king size bed, balcony overlooking the grounds and into the woods, includes 2 tennis courts, WiFi and is only minutes away from Windham and Hunter Mountain! Come enjoy all year round with hiking, mountain biking, kayaking, zip lining, snowboarding and skiing! **POOL OPENS MEMORIAL DAY 2023!

4.93 out of 5 average rating, 114 reviews

A gravel driveway leads through a green landscape with blooming purple flowers and lush trees. The chalet is positioned in the background, showcasing its rustic wooden exterior against a clear blue sky.

Guest suite in Windham

Cozy Cabin Condo by the Mountain, 5mins to skiing!

Steps from the Mountain! Just 1 mile away with a crisp mountain view, our beautiful chalet is a mere 5 minute drive from the slopes of Windham and just 15 minutes from Hunter! A short walk or drive from the charming town of Windham, you're perfectly located for a country getaway. The town itself is a wonderful mountain community with many great shops, restaurants and activities all within a short drive.

4.98 out of 5 average rating, 570 reviews

A modern kitchen space is highlighted by a knife rack displaying several knives mounted against a white subway tile backsplash. A decorative artwork featuring teacups is framed in wood and placed on the countertop, accompanied by a small potted plant with a textured appearance.

Condo in Lanesville

Trendy Condo Hunter Mountain

Newly renovated modern condo slope-side at Hunter mountain. Come enjoy the beauty of the Catskills & winter events while staying at our cozy and stylish condo. Warm up by the electric fireplace, fix a meal and have a drink in our brand new kitchen, watch a movie, and enjoy a restful sleep in a relaxing bedroom.

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Chalets

Adventure-ready homes with après-ski style

Houses

A space thats all yours, with room for everyone

Popular amenities for Windham vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Windham

4.99 out of 5 average rating, 94 reviews

Cabin in Windham

Modern forest retreat with hot tub and sauna

LindsayRating, 5 stars1 day ago

Great space for a weekend getaway with girlfriends. Beautiful, private location a short drive to Windham. Even though the house felt tucked away, it was easy to find thanks to clear pre-visit instructions.

4.85 out of 5 average rating, 54 reviews

Scenic Mountain Retreat • Hot Tub & Fireplace

NicoleRating, 5 stars3 months ago

This was the perfect AirBNB for a trip I took with 5 other friends! Richard was quick to response, answered all of my questions leading up to my trip and shared many recommendations. Easy and seamless stay!

Superhost

4.8 out of 5 average rating, 92 reviews

Chalet with HotTub 5 min to Windham, 15 min Hunter

LukeRating, 5 stars1 week ago

We had a great stay at Daniela’s place. Daniela was also very responsive when I had a question for her, which was much appreciated

4.88 out of 5 average rating, 73 reviews

A spacious living area is showcased, featuring a comfortable couch and armchair arranged around a central coffee table. Natural light fills the room through several windows, while a plant adds a touch of greenery. A dining area with wicker chairs is visible in the corner.

Condo in Hensonville

Cozy condo in Windham - Near Everything!

CarolynRating, 5 stars2 weeks ago

My husband and I attended a wedding and stayed here for 3 nights. It’s was such a lovely stay! A quiet street (with a street light right across the street), and a warm welcome as we entered the door. The place looked exactly as described and was a cozy place to land after the long days out. The shower pressure was also awesome and helped soak away the day. Anna was the perfect host! She made sure to let us know that we may not have service up there and that we should take down all the information in advance and was super proactive in all communication. We truly enjoyed our stay and would definitely stay here again if we’re in the area.

An outdoor seating area features two wooden chairs with white cushions and a matching bench. A rectangular wooden coffee table is positioned in the center, complementing the deck's light-colored flooring. Large glass doors provide a view into the interior space.

4.94 out of 5 average rating, 68 reviews

The Ski Ranch – 5min from Windham Mountain

MicaelaRating, 5 stars1 month ago

Such a beautiful space and property. We went for a girls weekend and all 6 of us had our own bed! We loved the interior design and the patio space looked really great although we couldn't use it because of snow in spring. Will definitely book again in warmer months!

4.89 out of 5 average rating, 55 reviews

The exterior of Mountain King Brewing Company is displayed, featuring a wooden facade with a shingled roof. A wooden sign with bold lettering announces the brewery. Lush greenery is visible in front, intermingling with the rustic architecture under a cloudy sky.

Apartment in Windham

Right on Main Street! 2mins to MTN

AnnaRating, 5 stars1 week ago

Great walkable location, especially for visitors taking the bus from NYC! Stephanie and her mom were very responsive and the place was great. I enjoyed working on the little balcony with a view of the mountain.