Fitness-friendly holiday rentals in Windham

4.98 out of 5 average rating, 160 reviews

Spacious Staycation near HITS & the Hudson

Pristine 3 BR, 2.5 bath ranch in a quiet cul-de-sac. 3/4 mile walk to the Hudson River and a 2 minute drive to HITS, village restaurants and shopping. Features a fully stocked open plan kitchen and skylit dining room, an oak bar, spacious living room and a sunny deck overlooking the fenced in backyard with a patio and a swimming pool. Large finished walk-out basement with washer & dryer, ping-pong, arcades,exercise room 65 in SmartTV & Wifi Split Units A/C & heat Gazebo with outdoor fireplace

4.99 out of 5 average rating, 102 reviews

Home in Lexington

Mountain View Chalet: Ski, Hot Tub, Firepit, Games

Spacious, peaceful lux cabin atop the Catskills. Enjoy mountain views, make smores, & soak in the hot tub. Catch up in the vaulted room by the fireplace w/ our wide game selection, while others watch movies downstairs. Host a dinner party with our fully equipped kitchen. Centrally located, 20 mins to 6 towns. Visit breweries, antique shops, dine, hike, fish, golf, or relax. Fast 600mbps internet. Perfect for groups, families, kids & pets. WFH, newborn, pet friendly. 3+ nights get discounted rate

4.98 out of 5 average rating, 182 reviews

Cabin in Phoenicia

The Woodland Valley Spa Cabin (20min to Woodstock)

Get away from it all and connect with nature at our luxurious cabin located right in the heart of the highly coveted Woodland Valley neighborhood of the Catskills. Conveniently located 9 min from downtown Phoenicia, 20 min from Woodstock for dining and culture, and 4 min from hiking trailheads. We painstakingly and lovingly designed the spa cabin, and if you come take advantage of all that it has to offer, we have no doubt you'll come away feeling rested, rejuvenated, and at one with nature!

4.91 out of 5 average rating, 231 reviews

Home in Hurley

Comfortable Woodstock Getaway

Our peaceful property is 5 minutes from the Town of Woodstock, 15 minutes to historic Kingston and Exit 19 of the NYS-Thruway, and 45 minutes to ski areas. The house is large and spacious with a fully equipped kitchen, plenty of lounge space, a sunlit expansive library with a large variety of old and new books, a home gym, and a backyard with a fire pit. Great for families with or without kids and weekend getaways with friends. Our goal is to offer an affordable experience for all our guests.

4.96 out of 5 average rating, 137 reviews

Home in Fleischmanns

Hog Mountain House Stunning Catskill Mtn Views

Stunning location and a beautiful contemporary ranch on plenty of land to roam. The views are breathtaking from the wrap around, decking equipped with outdoor furniture and propane gas grill. Interior has an open floor plan that includes a great room with a gas fireplace and a large kitchen that will entertain most chefs. Master bedroom w/full bath; including Sauna. 1 bedroom across from master and another upstairs w/private balcony. Laundry room downstairs. Finished basement w:mini gym.

5 out of 5 average rating, 148 reviews

Upstate Modern Scandinavian Barn in the Catskills

Renovated 1850's barn with 3 bedrooms and an ample loft space that can serve as a fourth. The house also has a large rec room with cathedral ceiling buttressed by hand-hewn beams, well-equipped kitchen, Scandinavian wood stove, sauna, home gym, and projector. Outside: 2 private decks with amazing views of Overlook Mountain, private grill, private hot tub. On property: shared tennis court, swing set, fishing pond, heated pool (summer only). 2 hours from NYC, 10 min. to Woodstock & Saugerties.

4.97 out of 5 average rating, 135 reviews

Peaceful Upstate Mountain Home with Soaking Tub

This mountain view home has it all. Sit on the porch, immersed in nature, and let the sound of Plattekill Creek serenade you. In summer months, grab a towel for a short walk to swim under a waterfall. In winter months, enjoy the view of Overlook Mountain while you sip your coffee at the farmhouse table. Work up a sweat in the gym using the multiple equipment options. When you are ready to enjoy delicious restaurants and unique shopping, drive 10 mins to the towns of Saugerties and Woodstock.

4.91 out of 5 average rating, 128 reviews

Shaggerties - fun cozy catskill mountain getaway

Cozy catskillS getaway at the bottom of northern escarpment. Waterfall view, swim pond right outside. Trail in backyard leading to creek, mountain views, treehouse w hanging swing chairs + giang jenga, jacuzzi & hammocks & badminton, firepit, outdoor speakers, private bathroom sauna w swim pond waterfall view, garage gym, 3 bedrooms including a fun bunkbed & foozball, the fun here is endless. Minutes from valleys, creeks, mountains, hikes, waterfalls, reservoirs, trails + AN AWESOME HOST :D

4.96 out of 5 average rating, 138 reviews

Cabin in Kerhonkson

Country- Hot Tub- Fire Pit- Game Room - Mini Golf

Welcome to our newly renovated countryside oasis on the Rondout Creek and Rail Trail in the Catskills, just minutes from Minnewaska State Park and the Gunks. Relax by the fireplace, hang in the speakeasy-style game room with pool, ping pong, and TV, or head outside to the fire pit, year-round hot tub, and mini golf under the stars. We offer private chefs, local meats, and recommendations for hikes bites, and watering holes. The home also features a gym/yoga room—and yes, we love pets! 🐾

Cottage in Livingston Manor

4.99 out of 5 average rating, 142 reviews

Cozy mountain top home - views, 5acres & a gym.

Located 2hrs from NYC, 7mins from Livingston Manor and close to Belleayre and Plattekill ski mountains. Sat atop a mountain, with 5 acres that sweep away from the property revealing stunning long distance views. Beautiful light throughout - front room with fireplace, full renovated kitchen, lounge, dining area, master bedroom, 1 large guest room, office / single bedroom, 2 bathrooms and huge covered back porch + a full home gym complete with Peloton bike, Peloton tread + ping pong table.