Holiday rentals in Bear Mountain

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!

Ranch in the Woods | A Peaceful Designer Retreat

Welcome to @ranch_inthewoods No cleaning fee STR permit #34035 This newly built ranch-style home with thoughtfully designed wabi-sabi interiors sits in the woods of the Warwick Valley. It's located a short drive away from several lakes, hiking trails, breweries, and dining experiences. It features forest/creek views, designer furniture, modern appliances (dishwasher, washer/dryer, gas cooktop), smart 4k TV, gym & yoga studio, gas firepit, and ample deck with an outdoor kitchen & dining area.

Secluded Hilltop Cabin near Beacon & Cold Spring

3 private acres atop small mountain. Feels like you're way upstate - check out the reviews! Hi-speed WiFi. Next to forest preserve and hiking trails. Furnished deck w grill overlooks Mt. Beacon sunsets. Loft w/queen and twin mattresses + pull out couch & twin-size mattress day bed on the porch. Perfect for 2, comfortable for 3, but 4 is probably max comfort since it's a small space. Please note that the road heading up there is steep. A car with AWD is ideal but a sedan will make it up too!

Boulder Tree House

Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

Luxury Cottage with Spectacular Lake Views

Ultra Chic Cottage set high above Greenwood Lake with Private beach and lake front community access. Minutes away from Mountain Creek Ski Resort, Spa & Water park, Mt. Peter Ski & Tubing, Warwick creameries, breweries & vineyards & apple picking. 1 BR, 1 Bath, play/office/common room. Huge wrap around fenced in deck with Mid century modern fireplace allows for scenic dining, lounging and around the fire gatherings. #LakeViewCottage_GWL Town of Warwick Short Term Rental Permit #P25-0245

The Greenwood Lake A-Frame: Perfect Lakefront View

Escape to a hip and cozy A-Frame cottage nestled right on Greenwood Lake, NY. Just over an hour drive from New York City, soak in the serene lake view, the quiet, and this unique retro modern A-Frame space. Perfect for a romantic couple’s getaway! Kick back and relax, listen to some tunes, read a great book, write your novel, sip your coffee, get creative, do some yoga stretches and enjoy time away from your day-to-day. Easy access to nearby beach, hikes, skiing. STR Permit #P25-0226

Spectacular Lake Views from Every Room & Garden

Our property boasts unparalleled views of Greenwood Lake and the mountains beyond. Our private garden features a seasonal waterfall cascading into a lily pond with fish and frogs. The shaded patio offers panoramic views and a gas grill. During the winter months, after skiing at nearby slopes, unwind in the claw foot tub or retreat to the cozy ambiance of our living room, with exposed wooden ceilings, a welcoming fireplace, a smart TV, a record player and board games.

Bedroom Forest View I Sauna I Fire-pit I Trails

Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

Half Moon: Fairytale Catskills Retreat

Enjoy nature in style at this fairytale in the forest. This idyllic escape combines whimsical structures, curated gathering spaces and a private wooded hillside surrounded by hiking trails and quaint towns. Disclaimer: This is a rustic cabin. Heating is from a wood-burning stove, there is no AC. The bath house is a separate structure from the cabin, up a hillside with stone steps. Cooking is via charcoal grills, small outdoor kitchenette or fire.

Willow Treehouse - secluded, unique, romantic

The Willow Treehouse is settled among the trees, overlooking a small, swimmable pond, on a wooded property 15min away from the town of Woodstock. It is cozy, yet has all you need to cook dinner, enjoy reading, sit on the couch and stare outside the window, or swim. No WiFi and no cell service = fully disconnecting from daily life and true relaxation. Perfect for couples and solo adventurers (2 adults max). STR operating permit #21H-109

Stunning 2-Bedoom A-Frame in the Woods with Sauna

Secluded Catskills A-frame with mountain views. Restore in the cedar barrel sauna, watch sunsets from the wrap-around deck, or curl up by the fire pit. Inside: lofty king suite, cozy queen, chef’s kitchen and dining, spacious lounge and soaking tub. Your elevated cabin escape awaits!

Old Mill Cottage - Upstate Mountain Views

Old Mill Cottage offers a perfect setting for an upstate getaway for 2-4 people. Enjoy an evening in, watching the sunset over the Gunx from the back deck or walk over to the The Ridge (by Millhouse Brewing). If you're more in to a night out, New Paltz is only 10 minutes away.