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

4.89 out of 5 average rating, 19 reviews

A spacious living area is highlighted by natural light streaming through large windows. Comfortable seating arrangements include a plush sofa and armchairs, while a coffee table sits in front of a cozy stone fireplace, complementing the warm wood accents throughout the room.

Cabin in Lackawaxen

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!

4.96 out of 5 average rating, 102 reviews

A rustic cabin nestled among vibrant autumn foliage features a sloped roof and stone chimney. Stacks of firewood are neatly arranged beside the porch, with a picnic table and a vintage vehicle parked nearby. Sunlight filters through the trees, creating a serene outdoor setting.

Cabin in Narrowsburg

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.

4.84 out of 5 average rating, 82 reviews

A charming two-story villa is set amidst lush greenery, showcasing light blue siding and large windows. A circular driveway leads to a spacious garage, while outdoor seating is arranged with four chairs near a small table, inviting gatherings in the serene surroundings.

Villa in Bloomingburg

Spacious 6BR Villa | Serene Scenic Mountain Escape

Escape to this spacious 6BR villa, a serene mountain retreat with scenic views. This peaceful getaway is perfect for families and groups. Located approximately 1 hour from the George Washington Bridge, it offers comfortable interiors, a well-equipped home, and ample outdoor space. Explore nearby hiking trails and relax in a tranquil setting just minutes from local attractions. Unwind and experience nature in every direction. Your peaceful mountain escape awaits—BOOK NOW FOR A SERENE GETAWAY!

Superhost

The interior of the spacious lakefront home is highlighted by large windows showcasing expansive views. A wooden table sits in the center of the living area, complemented by a stone fireplace. The outdoor deck extends towards the water, inviting tranquil moments by the lake.

Home in Lackawaxen

4.78 out of 5 average rating, 82 reviews

Magical Waterfront with 4-Season fun in Ski Resort

🌲 Lakefront Luxury Retreat in Masthope – 5BR, 4BA, Sleeps 15 Situated in the beautiful Upper Pocono Region, this spacious 4,000 sq ft lakefront home offers boating, fishing, swimming, horseback riding, mini-golf, gym, arcade, biking, hiking, leaf peeping, skiing, snow tubing, and more! Enjoy incredible lake views from every room, two expansive decks, a firepit by the water, and your own dock for boating and swimming. This home is designed for year-round getaways with family and friends.

A wooden deck is visible in front of a two-story lodge, surrounded by trees. Large windows reflect the twilight sky, and a pathway guides the viewer's attention to the inviting entrance. The landscape features a natural stone area, enhancing the serene outdoor setting.

5 out of 5 average rating, 22 reviews

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

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.

Superhost

A cozy sleeping area features wooden walls adorned with mounted deer heads and fishing memorabilia. A spacious bed is dressed in a neutral-colored blanket, flanked by two bedside tables with yellow lamps. A folded towel is neatly arranged at the foot of the bed.

Cabin in Monticello

4.8 out of 5 average rating, 5 reviews

Hot tub Bethelwood music

This charming three-bedroom cottage boasts a newly renovated and updated bathroom. Nestled in a tranquil neighborhood on a quiet cul-de-sac, it features a cozy fire pit with ample seating for six. A fenced-in yard, though small, provides the ideal safety space for any pets you may bring. Additionally, we welcome guests to enjoy a blowup pool with a chlorination floater, capable of accommodating up to six adults. A propane barbecue grill is also available for your culinary delight.

A comfortable living area features a brown leather sofa and a beige fabric sofa, arranged around a wooden coffee table. Natural light fills the space through large glass doors that lead to a screened-in deck, showcasing views of the surrounding forest.

5 out of 5 average rating, 5 reviews

Fall Winter Forest Retreat: Ski, Spa, & Sauna

A thoughtfully designed rural escape for solo travelers, couples, small families, and furry friends 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 the nearby artsy towns of our Pocono-Sullivan Catskill mountain community. Our on-site ski resort, Ski Big Bear, is a family-friendly mountain perfect for a crowd-free ski day (3 min drive from house).

Superhost

A bright living area showcases large windows that offer views of the outdoors, enhancing the natural light. A wood-burning stove is centered against a stone wall, while a TV is mounted above. A coffee table sits on a warm wooden floor, surrounded by cozy seating.

4.79 out of 5 average rating, 19 reviews

Masthope Chalet | 4 Bdrm | Firepit & Kayaks | A/C

This Masthope chalet is the perfect Pennsylvania escape, no matter the season. Boasting 4 bedrooms, 2 bathrooms, a wood-burning stove, workspaces, and more, this home has everything you need right at your fingertips. Spend the colder seasons hitting the slopes at Ski Big Bear, and on warm days, cool off at Westcolang Lake or one of the community pools. When the sun begins to set, grill dinner then gather by the fire pit to make s’mores and recount the day's memories with family.

4.98 out of 5 average rating, 49 reviews

An open living space showcases a wooden dining table set with plates and glasses, complemented by a cozy seating area. High ceilings adorned with exposed beams are visible, alongside large windows allowing natural light to fill the room. A staircase leads to an upper level.

Home in Lackawaxen

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!!!

4.87 out of 5 average rating, 109 reviews

The dining area features a wooden table surrounded by chairs, complemented by a floral-patterned tablecloth. A dark leather couch is positioned nearby, with a decorative cabinet showcasing various items. Natural light enhances the warm tones of the space, creating a cozy and welcoming environment.

Home in Livingston Manor

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.

The chalet features a spacious front deck surrounded by trees, providing a serene and natural setting. The wooden exterior combines with a red entrance door, leading to a two-story structure with a balcony on the upper level, enhancing the home's charming character.

5 out of 5 average rating, 49 reviews

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.