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Chalet holiday rentals in Bear Mountain

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Top-rated chalet rentals in Bear Mountain

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Top Guest favourite
Chalet in Prattsville
4.99 out of 5 average rating, 165 reviews

Designer Chalet with Sauna|Hot tub|Mountain View

Recognized as one of the Catskills’ most exclusive retreats, @lechaletcatskills is a modern-luxury escape where mountain serenity meets refined design. Set on 10 private acres near Hunter, Windham & Belleayre, this designer chalet invites you to unwind in style -think panoramic views, cedar sauna, hot tub under the stars & firepit for marshmallow nights. With a chef’s kitchen, curated interiors & nature all around, Le Chalet is the Catskills getaway your friends and family will be talking about.

Guest favourite
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, 246 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 favourite
A spacious living area features large glass doors that bring in natural light and provide views of the outdoors. Comfortable seating includes a modern sofa and armchair, accompanied by a coffee table and a dining area positioned nearby.
Chalet in Pine Bush
4.97 out of 5 average rating, 117 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, Ellenville and Blue Cliff Monastery. The location also provides convenient access to explore many of the Hudson Valley and Catskill towns and villages.

Top Guest favourite
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, 251 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.

Top Guest favourite
The exterior of the modern chalet is surrounded by lush greenery, showcasing a spacious sun room with large windows. A hammock is visible between trees, inviting relaxation. The property features a gently sloping yard leading down to the tranquil lakefront.
Chalet in Carmel Hamlet
4.97 out of 5 average rating, 119 reviews

Secluded Lakefront Chalet•Firepit•Yard Dogfriendly

Just over an hour from NYC, this secluded, dog-friendly lakefront chalet offers 200’ of private shoreline, fenced yard and sunroom with serene lake views. Thoughtfully styled with collected pieces from my travels, it blends quiet luxury with modern comfort. Cozy up by the fireplace, enjoy vinyl or a movie, watch snowfall, spot wildlife, explore nearby trails, unwind by the fire pit and rest in the king-size bed. Romantic, peaceful, beautifully secluded – your perfect winter lake escape awaits.

Guest favourite
Chalet in East Stroudsburg
4.98 out of 5 average rating, 265 reviews

Sauna | Hot Tub | Fire Pit | Hiking | Skiing

Relax and unwind at this stunning Poconos vacation property. Melt your troubles away with a dip in the hot tub or experience our custom-built Finnish-style sauna. This property has been thoughtfully remodeled throughout with warm wood floors, hand crafted ceramic tiles, extra comfortable beds, and custom artistic details, creating a truly unique and luxurious feel. Relax in the spa-like bathroom, sit by the firepit, or enjoy the lakes, pools, tennis courts or other amenities in the community.

Top Guest favourite
A sleek, modern outdoor area features a table lightly dusted with snow, surrounded by illuminated string lights. The glass walls provide views of a snow-covered landscape with trees and a flowing river, creating a serene winter atmosphere.
Chalet in Shandaken
4.97 out of 5 average rating, 226 reviews

Unique BellEayre River retreat

#2024-STR-AO-85 As seen in Chronogram magazine Chronogram/docs/chronogram-april-2023 High ceilings, Rough cut beams, All new HVAC and Hearthstone soapstone wood burning stove. Ping pong table. With Back deck tranquil getaway, you see and hear only the water flow with wrap around 4 season river right off deck. Close to scenic hiking, skiing, river tubing, and great restaurants along "Rapid Water"- The Algonquin Nation word for "Shandaken". Dogs welcome (Up to 2), sorry no cat

Top Guest favourite
The A-frame house showcases a striking design with a steeply pitched roof and large windows. A spacious deck extends across the front, offering a place to relax. Surrounding trees provide a sense of privacy, and vibrant foliage adds color to the scene.
Chalet in Saugerties
4.98 out of 5 average rating, 177 reviews

A-Frame Chalet in the Heart of the Hudson Valley

Set back on a private road surrounded by tall trees, The Chalet is a three bedroom, three bathroom A-frame house in close proximity to all the main attractions of the Catskills and Hudson Valley. Perfect for a weekend getaway or an extended stay, and great for couples and families. The house has three levels, each with its own bedroom, bathroom and common area. Relax by the fire pit, sip morning coffee on the deck, read a book in the loft, or take a walk in the woods.

Top Guest favourite
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
4.99 out of 5 average rating, 134 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.

Top Guest favourite
A back deck overlooks the scenic Catskill Mountain range, featuring a recessed hot tub and a fire pit. Soft lighting from string lights enhances the outdoor space, inviting relaxation while taking in gentle mountain views at sunset.
Chalet in Fleischmanns
4.99 out of 5 average rating, 254 reviews

Crows Nest Mtn. Chalet

Elevated into the Mountainside, Crow’s Nest looks out onto a spectacular view of the Catskill Mountain range of Belleayre. Grab a cup of coffee and watch the sunrise from the back deck or bask in the glow of the sunset while relaxing in the hot tub or hammock. This is an incredible place to unwind and take in that fresh mountain air or retreat to one of the many hangout spots in this newly renovated home. Follow us on IG : @crows_nest_catskills

Top Guest favourite
A unique three-story silo home is showcased, featuring a wooden exterior and numerous windows glowing warmly. Surrounded by snowy landscapes and trees, the structure is complemented by a wooden deck leading to an inviting red door.
Chalet in Willow
4.9 out of 5 average rating, 169 reviews

Cozy Silo Home w Mountain Views near Woodstock

The charming Willow Silo is nestled amongst the trees 10 minutes away from Woodstock and 15 minutes away from Phoenicia, this wondrous three story tower is well positioned to hiking nearby woods and mountains, as well as waterfalls. Wake up to a spectacular view of the mountain from the main bedroom or deck and end the evening stargazing from our own hammock by night. Secluded in the woods for a perfect relaxation retreat! ! PERMIT No: 23N-277

Top Guest favourite
A modern living room is presented with two comfortable couches adorned with soft throws and decorative pillows. Two dark coffee tables sit centrally on a textured area rug. Large windows offer glimpses of the surrounding trees, allowing natural light to fill the space.
Chalet in Gardiner
4.97 out of 5 average rating, 287 reviews

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.

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