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Cottage vacation rentals in Bear Mountain

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Top-rated cottage rentals in Bear Mountain

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Top guest favorite

A quaint cottage is nestled among trees, featuring a covered porch with a railing. Colorful seasonal flowers adorn the entrance, leading to a gravel pathway. The driveway is lined with trees and offers ample parking space, creating a serene atmosphere in a wooded setting.

Cottage in Cortlandt

5 out of 5 average rating, 203 reviews

The Little Cottage in the Woods

The Little Cottage in the Woods Nestled among the trees, and in close proximity to our main house, this studio cottage is newly refurbished, very private and is in a great location to access the Hudson Valley. Hiking trails are within minutes of the cottage or right out the front door. Golf courses are also minutes away. Whether you are in the area on business or just looking to escape for the weekend and enjoy the out doors. It is situated on 9 1/2 hikeable acres, all available to our guests

A striking wooden wall showcases a large bank of windows offering panoramic views of Lake Oscawana and surrounding foliage. The vaulted ceiling emphasizes the spaciousness of the room, inviting natural light to fill the space.

Cottage in Putnam Valley

4.89 out of 5 average rating, 281 reviews

Lakefront Cottage near Hudson Valley

Named in the Top 30 U.S. Lakehouse Rentals by Refinery29 in May'21, this beautiful, secluded cottage on pristine Lake Oscawana has breathtaking views. Escape the city and enjoy the fresh country air! Extra-large great room, cathedral ceilings, loft bedroom, kitchenette, bathroom, fireplace, wall of double-height windows with spectacular lake views. Central AC/heat, hardwood floors, private large deck with BBQ. Dock nestled in a cove where you can swim or paddleboard. Only 1 hour from NYC.

An open-plan kitchen and dining area features a large wooden table surrounded by several chairs. A modern kitchen with dark cabinetry and stainless steel appliances is seen in the background. A wood stove is positioned near the window, which offers views of the snowy outdoor scenery.

Cottage in Saugerties

4.94 out of 5 average rating, 309 reviews

New:Cozy Barn-Style Retreat Minutes From Woodstock

Recently featured in Vogue as one of “The Best Airbnbs in Upstate New York for a Weekend Away From the City” - A cozy getaway upstate on 2 acres of beautiful Catskill land. It's only 8 minutes to Woodstock, 5 minutes to the village of Saugerties, and there’s hiking, skiing and swimming within minutes. The entire second floor has been newly renovated including the bathroom and both bedrooms. The first floor is an open layout with kitchen, living and dining areas leading to the backyard deck.

A serene view of Walton Lake captures a wooden dock extending into calm waters. The setting sun casts a warm glow over the landscape, reflected in the lake. Lush greenery frames the scene, enhancing the tranquil atmosphere.

Cottage in Monroe

4.99 out of 5 average rating, 167 reviews

Cozy Lake Cabin

Make wonderful memories on pristine Walton Lake. 1 hr from NYC . This ALL INCLUSIVE Waterfront Cabin is like a mini resort! Rustic, rugged, off grid feel yet 2 miles from town. It has 2 docks, over water hammock & fire pit🔥. Enjoy sunsets on the covered porch & deck. Fish, & look for bald eagles🦅 Hungry? Paddle🛶 across the lake for tacos🌮 & drinks🍸. Inside has abundant retro & antique decor, modern appliances, fireplace♨️, & strong WIFI. Includes Free Firewood, NO CLEANING/PET FEES🐕

An outdoor area is illuminated by a vibrant red fireplace, surrounded by cozy seating arrangements with cushions and throws. Potted flowers add color, while string lights gently glow above, enhancing the serene atmosphere of the deck. A natural stone backdrop is visible in the distance.

Cottage in Greenwood Lake

4.98 out of 5 average rating, 349 reviews

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 #33593

Top guest favorite

A modern, two-story structure showcases large windows framed by climbing greenery. A stone pathway leads to a glass-paneled door, with potted flowers positioned along the entrance. The surrounding area is filled with trees, creating a serene atmosphere.

Cottage in Weston

4.97 out of 5 average rating, 151 reviews

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

A rustic cottage is nestled among tall trees, overlooking a flowing brook. A wooden bench sits on a grassy area, with large boulders nearby. The house features a deck and is surrounded by greenery, with a gravel driveway leading up to the front.

Cottage in New Milford

4.95 out of 5 average rating, 207 reviews

The Cottage on Babbling Brook

A cozy, rustic cottage beautifully overlooking Wimsink Brook. Custom designed & handcrafted woodwork throughout the home. An all around great spot for families and friends. A magical, peaceful and relaxing space. Conveniently located on the Connecticut/New York border, just a 1 ½ hour drive or metro north from NYC. The area is a prime location, as it offers some of the most stunning and scenic hikes & drives in the country. Only a 10 minute drive from Kent, New Milford or Pawling.

Top guest favorite

The image features a clear, inviting pool in the foreground, with the country home visible in the background. Surrounded by lush greenery, the house has a deck and large windows, blending harmoniously with the serene wooded landscape.

Cottage in Eldred

4.98 out of 5 average rating, 122 reviews

Bella Cottage w/Pool, BBQ - Catskill Getaway

Pool is now open! Pool temperate is set to 84 degrees Disconnect, relax and rejuvenate in this cute country home! Enjoy the serene, wooded surroundings as you watch deer trot by and end your day unwinding under starlit night skies. This 2-acre gem is tucked away on a private drive, just off the main road. Though secluded, grocery stores and restaurants are just down the street. The house is equipped with all the modern amenities to make your stay comfortable.

A cozy living room features a stone fireplace surrounded by plush seating. Wooden beams accent the ceiling, enhancing the rustic charm. Soft light glows from nearby rooms, creating a warm and inviting ambiance. Decor elements reflect nature-inspired design, adding character to the space.

Cottage in Kerhonkson

4.81 out of 5 average rating, 915 reviews

Cozy Cottage w/ Infrared Sauna

Escape to a serene, nature-inspired cottage nestled on the Shawangunk Ridge. Relax by the warm gas fireplace, gather around the handmade dining table crafted from 100-year-old reclaimed wood, or unwind in the private infrared sauna, accessible from the master bedroom. Explore nearby hiking trails, discover hidden messages throughout the space, and enjoy a curated "meaningful library." Perfect for relaxation, adventure, and meaningful moments with loved ones.

The living area features a 21’ tall wood-burning fireplace made of stone, complementing the vaulted ceiling and high skylights. A comfortable green sofa is positioned near a rustic coffee table, while a flat-screen TV is mounted on a wooden wall unit. Natural light floods the space.

Cottage in Pawling

4.98 out of 5 average rating, 132 reviews

Twin Lakes Designer A-frame Stone Cottage

*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.

Top guest favorite

The inviting exterior of a cozy cabin is surrounded by lush greenery, with warm lights illuminating the covered porch. A fire pit is featured at the forefront, surrounded by four Adirondack chairs, creating a welcoming space for evening gatherings.

Cottage in Kerhonkson

4.99 out of 5 average rating, 184 reviews

Ye Little Wood | Cozy Forest Cottage with Hot Tub

Stay at our comfortable and private 2-bed/2-bath home with covered porch, hot tub, fire pit, outdoor shower, and additional office cabin (perfect for work, exercise, or meditation) all surrounded by beautifully wooded forest. Centrally located in Kerhonkson just 15 minutes from local farm markets, popular farm-to-table restaurants and breweries, and hiking and other outdoor activities.

Top guest favorite

An aerial view showcases Amber Lake Cottage set against the backdrop of vibrant autumn foliage. The cottage features a spacious lawn leading to a dock on Amber Lake. Calm waters reflect the trees, while a rowboat rests nearby, indicating opportunities for outdoor activities.

Cottage in Livingston Manor

4.96 out of 5 average rating, 422 reviews

Catskills Modern Amber Lake Cottage

Featured in the NY Times, Amber Lake Cottage is nestled right on the bank of Amber Lake in Livingston Manor, NY. Just 2 hours from the bustle of your 9-5 in NYC, the home lets you catch your breath. Sleep in. Rowboat. Fix a drink by the fire. Dance to a record. Experiment with local produce in the chef's kitchen. See the stars above you. Hear quiet for the first time in months.

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Chalets

Adventure-ready homes with après-ski style

Houses

A space thats all yours, with room for everyone

Popular amenities for Bear Mountain cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

A charming cottage is framed by vibrant flowering shrubs and greenery. The front porch is adorned with decorative elements, while large windows invite natural light into the space. A wooden fence encloses the front garden, enhancing the quaint and inviting atmosphere.

Cottage in Great Barrington

4.93 out of 5 average rating, 301 reviews

Artist Cottage

A bright living area features a comfortable sectional sofa and a cozy armchair arranged around a central coffee table. Large windows allow natural light to fill the space, complemented by soft furnishings and a neutral color palette. A ceiling fan provides a gentle breeze.

Cottage in Greenwood Lake

4.82 out of 5 average rating, 215 reviews

Cozy Cottage | HotTub & Family Rm | 1H fr NYC

The spacious deck is softly illuminated by string lights, creating a serene atmosphere. A jacuzzi, elegantly positioned, offers a relaxing retreat, while surrounding trees provide a sense of seclusion as night falls.

Cottage in Monticello

4.9 out of 5 average rating, 124 reviews

Lovely Cottage w/ Jacuzzi+Woodstove!

Top guest favorite

A spacious outdoor deck is seen, featuring pink lounge chairs and a small black table with a decorative item. A shaded area with a red umbrella provides relief from the sun. Lush greenery and the tranquil lake are visible in the background under a clear blue sky.

Cottage in Greenwood Lake

4.98 out of 5 average rating, 120 reviews

Romantic Experience Secluded Lake House + Hot Tub

Top guest favorite

The outdoor space features a gravel area illuminated by string lights, creating a cozy ambiance. A round table with four red chairs is positioned under a green umbrella. Nearby, a hammock and a fire pit with chairs are visible, surrounded by natural elements like rocks and trees.

Cottage in Hawley

4.98 out of 5 average rating, 186 reviews

Hot Tub, Fire Pit, Minutes to Lake Wallenpaupack

Top guest favorite

The lakehouse is nestled among tall trees, with a spacious deck overlooking the water. Colorful flowers enhance the natural landscape, while a rocky shoreline leads to tranquil waters. Sunlight filters through the trees, creating dappled patterns on the house and surroundings.

Cottage in Highland Lakes

4.97 out of 5 average rating, 336 reviews

The Mountaintop Lakehouse that Time Forgot.

Top guest favorite

A hot tub bubbles softly amidst a serene lakeside setting. Two wine glasses rest on the edge, reflecting the lush greenery and calm water beyond. Tall trees frame the view, enhancing the tranquil atmosphere.

Cottage in Beach Lake

4.99 out of 5 average rating, 131 reviews

Driftwood Cottage on Welcome Lake-peaceful retreat

An outdoor fire pit is surrounded by several adirondack chairs on a grassy area. A stone wall frames the fire pit, with trees and a glimpse of a secondary building in the background. The scene reflects a serene natural setting.

Cottage in Bethlehem

4.98 out of 5 average rating, 113 reviews

Cozy Getaway | Pet Friendly | Litchfield Cty

Pet-friendly cottage rentals

A charming cottage is nestled among lush greenery, providing a serene entrance pathway. The driveway leads to the front door, surrounded by vibrant shrubs and trees that create a natural privacy barrier. The inviting exterior displays a warm welcome through its distinctive front door.

Cottage in Greenwood Lake

4.93 out of 5 average rating, 191 reviews

Cozy home in the Village of Greenwood Lake

A wooden deck is surrounded by lush greenery, featuring two lounge chairs positioned for relaxation. A charming cabin stands in the background, accentuated by a mix of trees and plants that create a secluded atmosphere.

Cottage in Carmel Hamlet

4.83 out of 5 average rating, 168 reviews

Lake Cabin Escape–Fenced Yard+Firepit.Dogs welcome

Cottage in Kingston

4.92 out of 5 average rating, 384 reviews

Kapitan’s Cottage: Private Retreat with Salt Pool

A charming cottage is set against a clear blue sky, surrounded by a lush green landscape. The pathway leads to a welcoming entrance with steps, while a wooden fence encloses the yard, creating a sense of privacy and tranquility.

Cottage in Kerhonkson

4.95 out of 5 average rating, 151 reviews

Catskills Country Cottage

Top guest favorite

The open living area showcases a cozy sofa facing a mounted television. A dining table is positioned nearby, with a modern kitchen featuring stainless steel appliances. Natural light fills the space through windows, highlighting the wooden accents and warm-toned decor.

Cottage in Boiceville

4.99 out of 5 average rating, 133 reviews

Magnolia Cottage

A wooden deck extends from the cabin, featuring a round table with two transparent chairs. The view includes a forest of bare trees under a setting sun, casting warm light across the space.

Cottage in Rhinebeck

4.93 out of 5 average rating, 292 reviews

Ridgetop 2 Br Cabin- Views, 130acre forest & falls

Cottage in Milford

4.86 out of 5 average rating, 369 reviews

forest cottage 1880s

The main living area showcases a cozy seating arrangement featuring a sofa and a lounge chair, positioned on a multi-colored area rug. A floor-to-ceiling stone fireplace serves as a focal point, and the open layout includes a kitchen area with modern appliances and a spiral staircase leading to the loft.

Cottage in Kerhonkson

4.88 out of 5 average rating, 235 reviews

Beautiful stream side cottage in the woods

Private cottage rentals

A charming tiny cottage features a front porch with white railings and hanging flower baskets. Windows are framed with black shutters, allowing natural light to shine in. The surrounding lawn is adorned with blooming flowers and greenery, creating a welcoming entrance.

Cottage in Gardiner

4.93 out of 5 average rating, 323 reviews

Tiny cottage on DiR mini farm

A serene view of the Delaware River is framed by bare trees along the bank. A pair of outdoor chairs is positioned close to the water's edge, surrounded by fallen leaves and grassy areas, inviting relaxation and appreciation of the natural setting.

Cottage in Matamoras

4.98 out of 5 average rating, 113 reviews

Lazy River Cottage on the Delaware River

A bright living area features a comfortable sofa set against a white wall, paired with a wooden coffee table. Large windows allow natural light to fill the space, while a patterned area rug adds warmth beneath. A modern chair and a small storage unit are also visible.

Cottage in Valhalla

4.96 out of 5 average rating, 295 reviews

Charming private 1BR apt. Easy access to NYC

A well-maintained cottage is framed by lush green grass and tall trees. A neat path leads to the front door, which is accented by a vibrant red door. The cottage overlooks a serene lake, enhancing its inviting exterior.

Cottage in Walden

4.96 out of 5 average rating, 110 reviews

Cute, Cozy, Lakefront cottage

The exterior of the Little Yellow Cottage features a charming yellow facade with white trim. A round window and a cupola add character to the roof. Surrounding greenery provides a natural setting, while a small white statue of a goat sits in front of the entrance steps.

Cottage in Highland

4.9 out of 5 average rating, 634 reviews

Little Yellow Cottage New Paltz - Kitchen wash/dry

The exterior of the cottage is framed by lush green grass and features two wooden loungers. Colorful flower beds and shrubs add natural beauty, while the rustic wooden facade complements the tranquil surroundings. Large windows invite light into the cozy interior.

Cottage in Woodstock

4.95 out of 5 average rating, 431 reviews

Woodstock Mountain Cottage

Top guest favorite

A light-filled living area is furnished with a cream-colored couch and a round glass coffee table atop a decorative rug. Green plants on either side add a touch of nature. A doorway leads to a separate bedroom area, enhancing the cozy ambiance.

Cottage in Warwick

5 out of 5 average rating, 221 reviews

Cottage at Millpond Falls - Romantic Luxury Escape

A cozy living area showcases a brown sofa adorned with decorative pillows, complemented by a patterned area rug. A rocking chair sits nearby, and a wooden table holds a stack of books. Natural light enters through two windows featuring bamboo shades.

Cottage in Phoenicia

4.95 out of 5 average rating, 291 reviews

Cozy Catskill Cottage on the Pantherkill

Destinations to explore