Chalet vacation rentals in Bear Mountain

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

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.

Cozy Poconos A-Frame on Appenzell Creek

Charming A-frame cabin with modern amenities on 3.5 acres of private land. Appenzell Creek and its tributaries run through the property. Perfect for a relaxing getaway. Minutes from Delaware Water Gap, skiing, hiking, state parks, lakes, water parks, outlet shopping, breweries, wineries, great dining, resorts, casinos and more. Enjoy listening to the rushing creek while grilling on the deck, soaking in the hot tub, decompressing in the sauna or dipping your feet in the creek.*NOT a party house*

Secluded Lakefront Chalet-Firepit+Yard Dogfriendly

⸻ Just over an hour from NYC, this serene, dog-friendly lakefront chalet offers 200 feet of private shoreline, fenced yard & sunroom with stunning lake views. Thoughtfully decorated with treasures from our world travels, it blends quiet luxury with modern comfort. Enjoy a king bed, fireplace, record player, TV. Dine by the water, relax in the lakeside swing, spot local fauna, hike the nearby trails & unwind fireside. Romantic, peaceful, beautifully secluded – your perfect summer escape awaits.

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.

Modern Mountain Chalet on 15 Acre Catskills Estate

This secluded "Frank Lloyd Wright" inspired home can be your own private mountain retreat and perfect haven for an escape from the city. Designed like a luxurious treehouse, the multi layers of porches and decks makes one feel as if they are sleeping in the clouds. The home offers rest and relaxation with the therapeutic effects of nature right at your doorstep and as a breathtaking backdrop. You'll be inspired by the beauty and peacefulness that awaits you from every corner of the home!

Spruced Moose Lodge w. Hot Tub & open Pool to oct

*Pool Open Until Oct 21!* Secluded log home nestled in 5 acres of Catskill mountain forest, with 4 bedrooms & 3.5 baths (incl. basement with built-in full size bunks). Enjoy a sunroom, screened porch, pool+ brand new hot tub, projection screen home theater & a treehouse that resembles a floating pirate ship 30 feet up in the trees. We renovated the kitchen & master bed with new walls of windows in May - pics to come! Town of Olive Registration No: STR-23-2 SEC-BLK-LOT: 52.4-1-5.500

Exquisite Chalet by Ashokan water, with generator

Recently renovated 3 bedrooms, 2 baths chalet for 6, one mile from stunning Ashokan reservoir views, on private lane but in the heart of Catskills, 10 min from Woodstock, Kingston and exit 19 off hwy 87, with fireplace, wraparound deck, deer-proof yard, firepit, barbecue, veggie garden. Ideal for couples, families, friends. Minutes to ski, ice climbing, iceskating, swimming, hiking, rock climbing, tubing, fishing, scenic walks, biking trails, food markets & excellent restaurants.

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.

Enchanting River Chalet

Located Conveniently in the Pocono's, just 1 hour 30 minutes from Manhattan and under 2 hours from Philly! Our relaxing 100 year old cabin has been fully remodeled down to the finest detail. Just minutes from the most popular hiking destinations, waterfalls, and sits right on the Bushkill River for great fishing and relaxation. The bathroom features special stone imported from Italy along with a custom carved rock sink. Pets are welcome free of charge (:

Serene & Bright: Minnewaska Mtn Views ~ Deck ~BBQ

Unwind in this bright newly renovated 3BR/2BA retreat tucked away in tranquil Kerhonkson. Enjoy Ulster County's attractions or relax on the private deck overlooking breathtaking scenery— just 2 hours from NYC & minutes to Minnewaska & Mohonk. ✔ 3 Comfortable Bedrooms ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Deck (Seating, BBQ, Views) ✔ Office ✔ Smart TV ✔ High-Speed Wi-Fi ✔ Laundry ✔ Free Parking The perfect escape for your upstate adventures!

Modern Zen Chalet at the Foot of Gunks w Mt. View

Kick back at the foot of the Shawangunk Mountains in this calm, stylish home. Surrounded by forest, the house features large picture windows in every room to help you reconnect with nature. Enjoy the natural stone porch with a fire pit and newly built barrel sauna. Located near Minnewaska State Park, with quick access to trails, and views of Millbrook Ridge and the Gunks’ iconic climbing routes right from the windows.