Vacation rentals in Hensonville

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Top-rated vacation rentals in Hensonville

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Guest favorite

Cabin in Maplecrest

4.95 out of 5 average rating, 241 reviews

The Cabin - Ski House near Windham

The Cabin is set back, secluded, unbelievably cozy and wonderfully romantic. It's a place to reconnect and recharge, to listen to the river and hear the wind through the trees and indulge in slow lunches and long walks and truly marvel at the Catskills. There's hiking in the summer, skiing in the winter, mountain fresh air and dark, starry nights. This is a house, and you can treat it as such. But if you let go, and give in to the energy of a space created with love, this will feel like home.

Guest favorite

Cabin in Maplecrest

4.93 out of 5 average rating, 196 reviews

Fraxinus House - Ideal for Windham & Hunter

Scenic country cabin located between Hunter Mountain and Windham Mountain, in the charming hamlet of Maplecrest. Surrounded by trees and the wilderness, it creates an idyllic mountainside escape, private and secluded grounds with only night stars and the sounds of wildlife. The decor is a mix of modern, color, and comfort, with lots of natural wood details. Both ski mountains are only a short 10 mins drive away. This is a great place for a romantic getaway or an outdoor trip in the Catskills.

Guest favorite

Townhouse in Windham

4.89 out of 5 average rating, 150 reviews

Amazing + pet friendly gem in the heart of Windham

Amazing 2 floor spacious getaway with A/C just minutes away from Windham Mountain ski resort, hiking trails, and great restaurants. Family friendly home with a large inviting living room, 2 spacious bedrooms, 2 full bathrooms and wood burning fireplace. Updated kitchen appliances, super-fast Wi-Fi and 3 smart TV's. Many extras including parking, 2 tennis courts, swimming pool and firepit. BBQ Grill on private back deck with scenic views. Winter season rentals preferred during Dec - March.

Top guest favorite

Condo in Windham

4.89 out of 5 average rating, 206 reviews

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.

Top guest favorite

Guesthouse in Windham

4.99 out of 5 average rating, 168 reviews

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.

Guest favorite

Chalet in Hensonville

4.97 out of 5 average rating, 99 reviews

Windham Immaculate Ski Chalet w / Awesome Fire Pit

Ultra Clean, Modern Chalet, Close to Windham Mountain, & a short scenic drive to Hunter mountain: An upscale, classic ski chalet: 4 bdrms and 2 full baths. Sleeps 8 Den & 3 bedrooms downstairs, complete with down comforters. 1 bedroom with a full size bed, 1 with 2 twin beds, 1 with 2 bunk beds & a full bath downstairs. Master bedroom is upstairs, with alcove area that would be great for a crib. Cathedral ceilings, large windows with mountain views fall & winter. NO PETS ALLOWED

Guest favorite

Home in Windham

4.95 out of 5 average rating, 66 reviews

The Hensonville Honeypot- HotTub/Game Room/Bikes

Located only 5 min to Windham/10 min to Hunter mtn!! Welcome to our newly renovated 5-bedroom, 4.5-bathroom farmhouse where rustic charm meets modern comfort. This fully remodeled home can accommodate up to 12 guests. With 2,400 square feet of living space in the home plus a newly converted barn into a game room / movie room, it's sure to have something to cater to everyone! The Hensonville Honeypot is your family's home away from home while visiting upstate New York.

Superhost

Condo in Windham

4.73 out of 5 average rating, 287 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!

Guest favorite

Townhouse in Hensonville

4.97 out of 5 average rating, 58 reviews

Spacious 2 Bdr. Townhome Minutes from Windham Mtn

Make this spacious, newly built townhouse yours during a relaxing getaway in the Catskill Mountains! Located just minutes from Windham Mountain, this 2 Bedroom/2 Bathroom townhouse is packed with amenities for you to enjoy your stay. Be sure to enjoy at least one of the many great restaurants just steps from the front door, spend some time at one of the breweries or wineries located less than 15 minutes away, and enjoy all that the Catskills has to offer!.

Top guest favorite

Cabin in Windham

4.97 out of 5 average rating, 110 reviews

5 Min to Skiing | Hot Tub | Fire Pit | Pool Table

Escape to this newly renovated mountain cabin just 5 minutes from Windham Mountain ski resort! With a private fishing pond and a deck offering panoramic resort views, it's a perfect outdoor retreat. Inside, enjoy a pool table, Pac-Man arcade, and shuffleboard for endless fun. A 2-minute drive to town makes dining and shopping convenient. The cabin's modern amenities, cozy fireplace, outdoor firepit, and hot tub guarantee a comfortable and relaxing stay.

Guest favorite

Cabin in Saugerties

4.98 out of 5 average rating, 214 reviews

Stunning 2-Bedoom A-Frame in the Woods with Sauna

Sleek 2‑BR A‑frame pairs timeless design with modern luxury in a secluded Catskills setting. Soak in the cedar barrel sauna after a day on the trails, then watch sunsets from the wrap‑around deck framing mountain views. Lofty king suite, cozy queen room, chef’s kitchen, bathtub, mudroom entrance, and office nook for remote work. Propane webber grill, smokeless fire pit, fast Wi‑Fi, and smart‑lock entry—your elevated escape awaits!

Top guest favorite

Home in Hunter

4.98 out of 5 average rating, 117 reviews

Lux Modern Cabin at Hunter Mountain

Modern private retreat in the heart of the Catskills with expansive views of Hunter Mountain that delivers an ultra-lux getaway experience. Casa Nevana is a brand-new construction. Enjoy each season of the Catskills in comfort and style. Immerse yourself in nature and slow living while experiencing luxurious accommodations and impeccable design. Follow us on IG @CasaNevana to see more of the home, local hot spots and more!