Chalet vacation rentals in Sullivan County

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Top-rated chalet rentals in Sullivan County

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Superhost

A wooden deck extends from the chalet, offering a view of lush greenery and rolling hills under a clear blue sky. Sunlight filters through the trees, creating dappled light on the ground. The vibrant colors of autumn foliage can be seen in the landscape.

Chalet in Grahamsville

4.94 out of 5 average rating, 181 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

Guest favorite

A chalet is nestled among tall trees, with a quaint exterior featuring dark and light wood accents. Two red Adirondack chairs are positioned around a stone fire pit, providing a cozy gathering spot. A spacious deck extends from the home, blending into the natural surroundings.

Chalet in Lackawaxen

4.92 out of 5 average rating, 396 reviews

Secret Getaway Nestled in a Woodland Setting

Welcome to your idyllic Pocono escape :) Our cozy yet chic home offers quiet surroundings of nature inside the amenity filled four-season community of Masthope! Perfect for families, couples & friends. Located less than 1 mile from community pools, restaurant, tiki bar, skiing & more. Lake and beach access just a short drive within the community! Whether you're looking to disconnect & recharge in the beauty of the Poconos - or ready to adventure all this area has to offer, it's a perfect match!!

Top guest favorite

The A-frame chalet is nestled among lush greenery, showcasing a rustic wooden exterior with an inviting wraparound deck. Natural stone steps lead up to the entrance, surrounded by various plants and trees, enhancing the tranquil setting typical of the Catskill mountains.

Chalet in Napanoch

4.95 out of 5 average rating, 240 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, 245 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.

Guest favorite

The cabin is framed by lush greenery, showcasing a wooden structure with a sloping roof and a spacious front deck. The surrounding area features a well-maintained lawn, dotted with trees and shrubs, offering a sense of privacy and seclusion.

Chalet in Claryville

4.85 out of 5 average rating, 235 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

An open-concept kitchen and living area features a large island with seating for eight, complemented by sleek black cabinetry. Bright light enters through multiple windows, illuminating the spacious layout that includes a comfortable seating arrangement and modern appliances.

Chalet in Monticello

4.84 out of 5 average rating, 124 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

The exterior of a charming black home is illuminated by soft yellow lights from the windows at dusk. A stone path leads through a landscaped garden area, which is bordered by planters. Multiple light sources create a serene atmosphere amidst the surrounding greenery.

Chalet in Callicoon Center

4.98 out of 5 average rating, 56 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

The exterior of the riverfront chalet is presented, featuring an A-frame design painted in soft green. Snow covers the ground, and evergreen trees surround the property. A wooden deck with chairs is visible, along with a porch light inviting a warm welcome.

Chalet in Monticello

4.98 out of 5 average rating, 121 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 cozy living area is highlighted by large windows allowing natural light to fill the space. A wood-burning stove serves as a focal point, with a plush sofa draped in a soft throw. A mix of plants and decorative items enhances the inviting atmosphere.

Chalet in Roscoe

4.96 out of 5 average rating, 126 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

A spacious porch area is featured, extending from the contemporary home with large windows. Verdant grass surrounds the exterior, while a breathtaking panoramic view of rolling hills and a clear blue sky fills the background.

Chalet in Obernburg

4.97 out of 5 average rating, 216 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.

Superhost

A spacious chalet is set against a dramatic sunset, framed by lush trees. The home features a mix of brick and stone elements, and a red roof adds a striking contrast to the natural surroundings. Well-maintained landscaping surrounds the property.

Chalet in Glen Spey

4.89 out of 5 average rating, 142 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!

Guest favorite

An inviting living area features a stone fireplace, flanked by large windows that provide scenic views. A combination of leather and fabric seating enhances comfort, while a rustic wooden coffee table sits at the center. Natural light fills the space, creating a warm atmosphere.

Chalet in North Branch

4.98 out of 5 average rating, 127 reviews

Catskills Mountain Chalet l 5 Star experience !

Stylish Chalet in the world famous Catskill mountains privately tucked away on 12 acres surrounded by wildlife and nature. Year-round outdoor activities, fine dining, breweries, and boutique shopping all nearby. Enjoy it all here at Clover Fields! Why "Clover Fields" you ask? Deer visit our property almost daily to graze on our sweet clover fields. It's not uncommon to see them throughout the day. Other notable guests: fox, various birds, woodchucks, chipmunks.