Chalet vacation rentals in Sullivan County

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, Ellenville and Blue Cliff Monastery. The location also provides convenient access to explore many of the Hudson Valley and Catskill towns and villages.

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.

Architecturally Unique 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!

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.

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 is cozy with rustic charm and is the perfect getaway nature-lovers. Outdoor enthusiasts will love the many hiking trails and waterfalls just a short drive away. A sanctuary for goats, animal lovers can visit with over 30 rescues during their stay. Art materials and yoga mats are provided to round out a perfect escape for you to unwind, rest, relax and heal.

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.

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.

Secluded cabin in Catskills yoga retreat

A beautiful peaceful secluded cabin and 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 take a cool outdoor shower. Great yoga retreat. There is a whole flourishing ecosystem there with family of rabits, foxes, humming birds, bees, butterflies and birds , flowers…A place for hiking lovers and Yoga retreat. Detox from your technology

Secret Getaway Nestled in a Woodland Setting

Welcome to our Pocono Mountain escape!! Perfect for families, couples & friends! Less than 1 mile from pools, restaurant, tiki bar & skiing!! Our cozy home provides surroundings of nature while staying close to fun. Located in Masthopes' amenity filled four-season community - Lake and beach access just a short drive!! If it's a need to disconnect & recharge or if you are seeking adventure here in the beautiful Poconos, let our happy spot be your home away from home too! :)

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.

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.

Au Bon Orchard - Hot Tub - 56 Private Acres

Au Bon Orchard is nestled between some of the Catskills most popular destinations like Roscoe, Liberty and Livingston Manor; you will find Au Bon Orchard. - 2 Hours from NYC - Infiniti Pool (May, Post Memorial Day - Mid September) - Hot Tub - EV Car Charger - 56 Private Acres - Private Waterfall - Catskill Mountain Views - Close to: Neon Croissant, The Smoke Joint, Livingston Manor, Liberty - 3 Beds 2 Bath