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

The open concept living area is observed from above, featuring a spacious dining table surrounded by white chairs. Large windows invite natural light and views of the surrounding greenery. A gray sectional sofa and a television are positioned in the corner, creating a welcoming atmosphere.

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

Chalet in Pine Bush

4.99 out of 5 average rating, 82 reviews

Spacious A-Frame Getaway near Hiking and Wineries

Escape to our A-frame in the heart of the Shawangunks, nestled within the picturesque Hudson Valley. Just 1.5-2 hours from NYC, our spacious and serene home is perfect for a peaceful retreat, outdoor adventures, and exploring local wineries. Nearby attractions include Lake Minnewaska Park, Mohonk Preserve, Sam’s Point, the Shawangunk Wine Trail, Legoland, and Blue Cliff Monastery. The location also provides convenient access to explore many of the Hudson Valley and Catskill towns and villages.

Top guest favorite

The exterior of the chalet features a modern blue facade with large glass doors opening to the deck. A stone fire pit surrounded by adirondack chairs is positioned on the grassy lawn, offering a cozy spot for outdoor gatherings.

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

Chalet in Claryville

4.84 out of 5 average rating, 225 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

The open concept living space features a high ceiling with recessed lighting. A central kitchen island is surrounded by stylish seating. An electric fireplace is located on the wall, and large windows provide ample natural light. A staircase is visible leading to the loft area.

Chalet in Monticello

4.86 out of 5 average rating, 111 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 outdoor space features a cozy firepit area surrounded by six adirondack chairs, inviting gatherings under soft evening light. The backdrop includes a warm-toned house with a porch, nestled among flowering trees and green foliage, creating a peaceful retreat.

Chalet in Callicoon Center

5 out of 5 average rating, 47 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!

Superhost

Chalet in Forestburgh

4.85 out of 5 average rating, 13 reviews

Serenity at Lake Joseph | Lakefront•Hot Tub•Ski

Welcome to your Serenity at Lake Joseph. This lakefront getaway has all the amenities you could dream of surrounded by a 2000 acre forest preserve with a private hot tub. No detail was overlooked in this cozy, but luxurious 4 BR, 4 BA home with incredible views of the lake. 1.5 hours from NYC, only 15 minutes to the new Holiday Mountain Ski & Fun Park, 15 minutes to Resorts World Catskills, near several hiking trails, local breweries, and 20 minutes to Bethel Woods Center for the Arts.

Guest favorite

An inviting living area features warm wooden flooring and angled walls, with a cozy sofa and unique seating. A dining space is visible, showcasing a small table and modern chairs. A spiral staircase leads to an upper level, enhancing the spacious layout.

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 semi-private loft space is adorned with warm wooden beams and large windows, allowing natural light to fill the area. A comfortable chair and ottoman sit next to a small side table, inviting relaxation. A ceiling fan provides a breezy touch.

Chalet in Roscoe

4.97 out of 5 average rating, 116 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, 207 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.