Ski-in/Ski-out holiday rentals in Sullivan County

Cozy Cabin at Ski Big Bear Mountain in Masthope!

Come stay at our cozy, all-season Poconos mountain cabin! BBQ with the family on the back deck, make s'mores by the fire pit, sip tea on the front porch or read a book on the unique loft space. Only 5 min from Ski Big Bear for snow tubing, cross country ski, and more. In summer tan on the beach at the lake, kayak, ski or motor boat. Enjoy a cocktail by the outdoor pools near the tiki bar while kids play mini golf. You can also, hike, tennis, bike, workout at gym, horse ride or visit petting zoo!

Quiet Path Haven

Welcome to Quiet Path Haven, clean, peaceful home, perfect for families, long stays, and remote work. Enjoy tree🌳 views with deer🦌 and birds🐦. Morning espresso ☕ on the balcony, basement games. Cozy up in the living room with movie nights with home cinema setup🎦. Office work table for remote work and business travelers who need focus, space and peace. Outdoor walks, and BBQ grill. Quiet neighborhood with friendly neighbors, plus great local food and shops nearby. Your Home🏡 away from home

Catskill's Le Petite Cabine on the River

The Cabine is an authentic Catskill's old fashioned experience. Hand built stone fireplace & wood stove charm in this 1955 timber frame 2 bedroom Cabine. Open year round...winter ski & ice fishing season. Privacy & your own frontage on the bucolic Ten Mile River trout stream. Wooded seclusion from neighbors yet 5 min. from town. Several campfires, writer's guest shack, nearby quaint Narrowsburg hamlet & Delaware River. Seasonal hot outdoor shower design, overlooking river & natural surrounds.

Spa & Sauna Four Seasons Retreat: Ski, Pool, Lake

Little Norway PA is a thoughtfully designed rural escape for solo travelers, couples, & small families within a few hours from NYC & Philly. Enjoy our ¨tiny spa¨ without the price tag of nearby Woodloch: whirlpool & Finnish sauna all to yourself in the surrounding forest. Enjoy nearby artsy towns of our Pocono-Sullivan Catskill mountain community. Guests receive 25% off lifts at our on-site mtn, Ski Big Bear. Awesome summer amenities include: two pools, mini golf, lake beach, and more

The Flying Dutchman Cottage in Masthope /Poconos

Completely renovated cozy cottage, in the middle of beautiful woodlands (deer visiting our garden every day!), lots of privacy, in the amenities-filled upscale Masthope community (with Ski Big Bear at Masthope Mountain). Relax with the whole family at this peaceful place to stay. Amenities offered by the community; Ski Big Bear Tennis Volleyball Basketball Playground Restaurant Bar Heated pool Sandy beach Spring-fed glacier lake Horse Stables Miniature golf Insta @FlyingDutchmancottage

Chalet w Pool table, Arcades & Lake, Pools, Ski

Escape to our charming chalet that offers lake, pool, and ski resort access in a four-season wonderland. Relax by the fireplace, cook in the fully-equipped kitchen, and enjoy wildlife sightings. Swim in the lake, take a dip in the pool, or hit the slopes for thrilling skiing. This retreat is a nature lover's paradise, with nearby trails for hiking and biking. Conveniently located, it's the perfect getaway for relaxation and adventure. Book now for an unforgettable four-season experience!

4 Bedroom Farmhouse in Ellenville, NY

Farmhouse on 100+ acres and a lovely calming stream, with pools and 3 smaller dams around the property. Located outside of town but easy access to stores and restaurants, high speed internet and great cell reception. Near several reservoirs with great swimming holes, hikes, and camping grounds. Only 2 hour drive from NYC! Great large back deck, equipped with a BBQ grill, and a scenic view of the woods. Features amazing out door showers, wood-burning sauna, and a small fire-heated hot tub.

Ski in/out next to Bunny Hill @Ski Big Bear PA

Take it easy at this unique and tranquil getaway in the Pocono Mountains. Little Bear Lodge is located at the top of Ski Big Bear - walking distance (5 minutes) to the communities primary recreational complex. This ski in/out home was recently remodeled ready for you to create everlasting memories. Wake to amazing Mountain Views as you drink your coffee or tea overlooking Ski Big Bear. We’d love to share our beloved vacation home we recently remodeled with you and your family.

25% off ski lifts 5 min walk to ski lodge & pub

Discover the best of the Poconos when you stay at this peaceful and pristine home. Our Little Haus is located in the heart of the lovely 4 seasons amenity haven Masthope Community. Super short walk to Ski Big Bear, Lodge, Pools, Tiki bar, Restaurant and much more! There's adventure for all guests to enjoy! This home is perfect for family and friends, for a couples romantic getaway, or working remotely. Your beautiful memories are awaiting :) Book today!!!

"Cozy Upstate Retreat” 3bedroom 2bathroom

Relax with the whole family at this peaceful place to stay. ✨ Cozy Barryville Escape | Year-Round Adventure ✨ Welcome to your perfect Upstate getaway! Our cozy retreat is nestled in the heart of Barryville, NY—just steps from local restaurants and only minutes from the magical town of Callicoon. ☀️ Summer Fun: Go kayaking on the Upper Delaware Scenic & Recreational River ❄️ Winter Adventures: Hit the slopes nearby for snowboarding and skiing

Cottage by the River

Cozy country home located in the Catskills. It is perfect for a weekend getaway. Walk out to river views and multicolor leaves an ideal fall setting. Fire pit and wood on site to make a fire at night and enjoy the stars.  There is a small town and local breweries only 5 minutes away. What the siding lacks, the fully renovated inside will surely not disappoint. There are four bedrooms and two bathrooms that will comfortable fit up to 10 guests.

Bella Vista Chalet Poconos - Ski Resort

Welcome to Bella Vista Chalet, a Four Season Resort located in the heart of the Masthope Mountain Community in the Northern Poconos. Offering year round activities, in winter you can enjoy Ski Big Bear Mountain, Skiing, Snowboarding and Snow tubing, or just cozy up to the wood fireplace and stay warm. By summer enjoy the peaceful surroundings on the porch, take advantage of the lake access for a swim or enjoy the outdoor pools and slides.