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

Find and book unique ski-in/ski-out homes on Airbnb

Top-rated ski-in/ski-out rentals in Sullivan County

Guests agree: these ski-in/ski-out homes are highly rated for location, cleanliness, and more.

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Guest favorite

Cabin in Lackawaxen

4.93 out of 5 average rating, 15 reviews

Cozy Big Bear Mountain Ranch at 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!

Guest favorite

Cabin in Narrowsburg

4.96 out of 5 average rating, 97 reviews

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.

Guest favorite

Home in Lackawaxen

5 out of 5 average rating, 6 reviews

The Flying Dutchman Cottage Masthope -quiet street

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

Guest favorite

Home in Lackawaxen

5 out of 5 average rating, 26 reviews

Poconos Masthope 6BR Home Ski Big Bear - Lake Pool

Large contemporary 6 bedroom, 4 full bath. Home located inside a premier private community ( Masthope ). Community offers reduced pricing to Ski Big Bear. Also offers 2 swimming pools w/ dive boards & splash pads, playgrounds, horse stables, petting zoo, fitness center, mini golf, and basketball courts. Located in the Poconos, there are additional opportunities for entertainment within a close proximity that includes water parks, camping, hiking, fishing, biking, shopping & fine dining.

Guest favorite

Chalet in Lackawaxen

5 out of 5 average rating, 9 reviews

Ski in/out closest home to Lodge in Masthope

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.

Guest favorite

Cabin in Lackawaxen

4.97 out of 5 average rating, 65 reviews

Modern Cabin nestled between Catskills and Poconos

Welcome to our cozy cabin tucked away between the Catskills and the scenic Upper Delaware River, within a 2 hour drive from NYC. Perfect space for a getaway. The cabin is comfortably suited for 2-4 people. It's close to many attractions all year round (lake, skiing, winery, luxury spa) and it is a convenient and easy drive to the delightful hamlets of Narrowsburg, Milford and Hawley, bursting with fun things to do as well as amazing places to eat and shop.

Guest favorite

Home in Lackawaxen

4.97 out of 5 average rating, 34 reviews

5 min walk to Ski Lodge and Pub 25% off Ski Lifts!

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!!!

Home in Lackawaxen

5 out of 5 average rating, 3 reviews

Pocono 4 bdrm Eagles Nest Retreat Masthope

Forget your worries in this spacious and serene space conveniently located in the private Masthope Mountain Community. Just a 5-minute drive to either the lake/beach or the pools/top of the mountain where you can also enjoy skiing in the winter. This home has year-round amenities only minutes away within the community. A quick 15 minute drive away is the award winning Woodloch Resort where you can play a round of golf or enjoy their 5-star spa!

Guest favorite

Home in Livingston Manor

4.86 out of 5 average rating, 103 reviews

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.

Guest favorite

Chalet in Lackawaxen

5 out of 5 average rating, 34 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.

Guest favorite

Villa in Bloomingburg

4.83 out of 5 average rating, 47 reviews

6 BR Mountain Villa/Serene Nature/near Legoland

Discover Mountain Serenity in our spacious and upgraded home. Immerse yourself in nature's embrace, whether stargazing from the patio or exploring nearby trails. Create memories of peaceful mountain escapes with friends and family, approximately 1 hour from the George Washington Bridge. Forget your troubles – your peaceful retreat awaits.

Superhost

Chalet in Callicoon

4.83 out of 5 average rating, 239 reviews

Bethel Woods Majestic Rolling Hills AFrame w Views

Just a little over 2 hours from New York City and minutes from Bethel Woods Arts Ctr. The open farmland and rolling hills of Callicoon NY are the perfect upstate getaway for those seeking the best of country living. Nature lovers, cooks, hikers, outdoors fanatics & gardening enthusiasts this is your spot.