Chalet vacation rentals in Bear Mountain

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

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

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*

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.

Lakefront Chalet~Kayaks~Sauna~Fire Pit~Fireplace

Escape the ordinary and step inside our modern chalet, a true lakefront with private access to the Emerald lakes. Unwind by our private beach or sundeck. The natural light, pine trees and panoramic views of the lake, all make it a peaceful place to relax and enjoy some time with your loved ones. Our modern kitchen is fully equipped to cook a chef’s meal and feast on laughter and memories around the rustic table. Later, relax by the crackling fire on the beach. Welcome to our lakehouse.

Secluded Chalet w/ Unforgettable Views on 22 Acres

A nature-lover's oasis, this 3-bedroom/4-bed/2-bath log-built chalet with contemporary furnishings is perched high along the northernmost edge of the Catskill Mountains offering unforgettable panoramic views from inside and out across 22+ secluded acres. Due to its proximity to hiking trails, lakes, rivers, breweries and wineries as well as Windam (7 mi), Hunter (16 mi), Catskill (26 mi) and Hudson (29 mi), this is the ideal location from which to explore the best the Catskills has to offer.

Spacious cabin w/grill, firepit & mountain views

NOTE: Click “Show More” to read the full description. Home with stunning views perfectly situated between Roxbury and Stamford! Drink your morning coffee at the bar on the deck overlooking the mountains, curl up with a good book in the reading nook, or explore the farms, mountains, and countryside of the beautiful Western Catskills. Cabin is situated on five beautiful acres at the end of a private drive. Beautiful sunrises over the mountains, with wide-open stargazing after dark.

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 (: