Chalet vacation rentals in Sullivan County

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Top-rated chalet rentals in Sullivan County

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Top guest favorite

Chalet in Lackawaxen

4.97 out of 5 average rating, 121 reviews

Serene Mountain Haven at Masthope

Masthope Mountain Community, is a beautiful community and our home is ready to welcome you no matter what the season. By winter you can ski, snowboard and snow tube, or just cozy up to the gas fireplace and stay warm. By summer you can enjoy the peaceful surroundings on the porch, WALK down to the lake for a swim, enjoy one of the two community’s pools or just relax at the Tiki Bar. AMENITIES WILL NOT BE AVAILABLE TO RENTERS JULY 4, 5,6 & 7! (This includes but not limited to pool/beach/lake)

Superhost

A spacious dining area presents a long wooden table set with decorative items, including candles and a tray. Large windows allow natural light to fill the room, while a view of greenery is visible outside. A modern chandelier hangs above the table, enhancing the ambiance.

Chalet in Grahamsville

4.95 out of 5 average rating, 171 reviews

Catskills mountain view chalet

Come and enjoy our Catskills mountain view chalet. Escape the chaos of the city for peace and serenity. In our home you'll find an open concept kitchen/dining and living room space, a huge deck, 2 bedrooms, a newly renovated bathroom and a loft work space. Take in the country skyline view with a glass of wine on the deck while listening to meditative sounds of the babbling brook. Don't forget to bring groceries as the best way to enjoy the chalet is with a home cooked meal with those you love

Top guest favorite

Chalet in Napanoch

4.95 out of 5 average rating, 231 reviews

Catskills Aframe, Water View, Goat Sanctuary

This charming Aframe is tucked into the Catskill mountains, with spectacular seasonal views of the Rondout Reservoir. This house has a cozy feel with rustic charm and is the perfect getaway for those wishing to escape to nature. Outdoor enthusiasts will enjoy numerous local hiking trails and we're just 25 minutes from popular areas such as Mohonk Preserve, Sams Point, Minnewaska. A goat sanctuary, animal lovers can visit with our over 30 rescue goats, chickens, dogs and of course, local wildlife

Top guest favorite

A modern living area is showcased, featuring a plush dark sofa and a live-edge coffee table at its center. Large sliding glass doors provide expansive views of the surrounding landscape, while polished concrete floors complement the wood-paneled ceiling. A flat-screen TV is mounted for entertainment.

Chalet in Cragsmoor

5 out of 5 average rating, 241 reviews

Scandinavian-Style Chalet with Scenic Views

Wake up to hilly views from this Scandinavian-inspired chalet boasting wood-paneled cathedral ceilings, sharp furnishings, and concrete floors. Share a glass of wine with a friend beside a sleek fireplace and live-edge coffee table in a chic living area. Please inform the host if you plan to bring a dog as there is a 15 pound weight limit. Maximum number of guests/visitors/people permitted on the property is 2. The owner lives on the property and is available for anything guests may require.

Superhost

A charming log cabin is nestled among lush greenery on a spacious lawn. A wooden deck extends from the front, complementing the structure's rustic appeal. Surrounding trees provide a natural backdrop, enhancing the peaceful setting in the Catskill hills.

Chalet in Claryville

4.84 out of 5 average rating, 224 reviews

Secluded Cabin in Catskills Park on 20 acres

It's a secluded cabin and we kept it small and pristine for a reason. We also just planted cherry trees and apple tree...We kept it pristine so one can feel nature. And we dont have internet or Tv there otherwize it would be like being in the city. Get a feel for what it is like to be in a cabin in the woods. There is a whole flourishing ecosystem there with family of rabits, foxes, humming birds, bees, butterflies and birds. We are planting a garden and flowers. A place for hiking lovers.

Superhost

A wooden deck extends towards a serene body of water, framed by tall trees. The calm waters reflect the surroundings, while several boats are docked nearby, creating a peaceful atmosphere for relaxation.

Chalet in Monticello

4.85 out of 5 average rating, 108 reviews

Modern Chalet with Hot Tub and Lake Access

Spacious home with gorgeous decks, patio areas, and hot tub, presented by StayBettr Vacation Rentals. Shared dock access is available across the street. Indoors you will discover cathedral ceilings, fireplace, and a large eat-in kitchen and living room area your group to come together. New whole house water filtration system recently installed. The entrance to the home has a ramp for accessibility, and the home has wide corridors and interior doors, so all can be included on your vacation.

Top guest favorite

Chalet in Callicoon Center

5 out of 5 average rating, 45 reviews

Architecturally Designed Catskill Chalet

Unwind in a secluded upstate escape on 6+ wooded acres off a dead-end road while relaxing to the sound of Callicoon Creek. This newly renovated and thoughtfully designed home has multiple lounging areas, a wood-burning fireplace, hot tub, and fire pit. We are less than 15 minutes from the most charming Catskill Main Streets of Livingston Manor, Roscoe, Jeffersonville, and Callicoon and a five-minute walk to Callicoon Hills for dinner or coffee. Bring your family + dog out to the country!

Top guest favorite

A hot tub is situated under a covered area, illuminated with vibrant purple lights. Beyond, a fire pit surrounded by chairs can be seen, with the soft glow of evening light filtering through the trees, which creates a serene outdoor space.

Chalet in Lackawaxen

5 out of 5 average rating, 36 reviews

Chalet with hot tub fire pit skiing in the Poconos

Welcome to our charming chalet in the heart of the Poconos—your perfect spring escape! Just a quarter mile from the scenic Delaware River and minutes from hiking trails and lakes, this cozy retreat offers endless opportunities for outdoor adventure. Spend your days kayaking, fishing, golfing or exploring nature spots, then unwind in the hot tub or gather around the fire pit for evening s’mores under the stars. With amenities for comfort and fun, our chalet is your ideal spring sanctuary!

Guest favorite

A spacious living area features wooden beams and warm lighting. A large brown sectional sofa is paired with a patterned armchair, creating a comfortable seating arrangement. A colorful area rug complements the hardwood floor, while an open staircase leads to the upper level.

Chalet in Monticello

4.98 out of 5 average rating, 118 reviews

Riverfront Ski Chalet

Escape to the country air at Sean & Brad's riverfront chalet on the Neversink River. Formerly a popular ski shop and yoga studio, this fully renovated property offers you every possible amenity. Walk across the street to launch your kayak or toss a line into some of the best trout fishing around, roast s'mores around the fire or visit the Resorts World Casino, just 5 minutes away. Golf, hiking, mountain biking, local breweries and distilleries...all just a short distance as well.

Guest favorite

A high-angle view of the main living space reveals vaulted wooden ceilings and large windows. The open layout features a dining area with a large table and a cozy seating area next to a wood-burning stove. Sliding glass doors provide access to the outdoor deck.

Chalet in Roscoe

4.96 out of 5 average rating, 114 reviews

Sunday Mountain House - Cozy Catskills Chalet

Sunday Lodge & Mountain House is a peaceful retreat on 5 acres in the Catskill Mountains. Our home is located about 2-2.5 hours from NYC, and minutes from the charming towns of Roscoe and Livingston Manor. Tucked away on a mountain road, this is the perfect a place to relax and unwind. You can sleep. You can sip. You can cook. You can workout. You can hang. Outside of our doors you can fish. You can hike. You can stargaze. You can play. A place to do everything or nothing at all.

Top guest favorite

The exterior of the contemporary home is showcased against a vibrant sunset, highlighting the rooflines and expansive windows. Lush green grass surrounds the house, leading to panoramic views of the distant mountains and valleys in the background.

Chalet in Obernburg

4.97 out of 5 average rating, 205 reviews

King Of The Hill

Romantic Mountain Top Retreat with Million Dollar Views Escape to this incredibly private, mountaintop vacation home, nestled on 80 acres of pristine land. Offering breathtaking, panoramic views. This peaceful retreat is the perfect getaway for relaxation and romance. Just 2 hours from the GW Bridge, enjoy the tranquility of nature without sacrificing modern comforts, including high-speed internet service. The ideal escape for those seeking both privacy and convenience.

Guest favorite

A tranquil pond surrounded by lush greenery reflects the vibrant colors of sunset. Large stones line the water's edge, and the scene is complemented by trees in the background, enhancing the natural beauty of the setting.

Chalet in Glen Spey

4.9 out of 5 average rating, 132 reviews

Mayflower - Lake access/hot tub/game room/pets

Only 1 1/2 hours from NYC! Come and take in the winter beauty in the Catskills. Welcome! Everything you’d ever want in a lake community chalet! Please bring all your favorite people and enjoy our 3500ft² chalet and an acre of fenced in gorgeously landscaped grounds complete with firepit, fruit trees, fishpond, hot tub, outdoor pizza oven, ultimate game room and best of ALL a 5 minute walk down our private treelined road down to your own private 30 feet of lakefront!