Cottage holiday rentals in Bear Mountain

Find and book unique cottages on Airbnb

Top-rated cottage rentals in Bear Mountain

Guests agree: These cottages are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
Guest favourite
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, 260 reviews

Beautiful stream side cottage in the woods

Stunning fully renovated 1970 partial A frame cottage in the woods! Set privately on four acres with a stream and meandering stone walls, the cottage is modern yet rustic, with a mid century decor. Main floor has living room with beautiful floor to ceiling stone fireplace (gas operated), kitchen, bathroom, and an office with a desk and twin bed. Second floor has master bedroom with queen size bed and a separate loft area with desk. Great place to relax in nature - a perfect couple's getaway!

Top Guest favourite
A soft, textured sofa in a light neutral tone is positioned against a warm, smooth wall. A single floor lamp provides gentle lighting beside a small black side table. An adjacent window is dressed with sheer curtains, allowing natural light to filter softly into the space.
Cottage in Warwick
5 out of 5 average rating, 106 reviews

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.

Top Guest favourite
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, 214 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

Guest favourite
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
4.89 out of 5 average rating, 673 reviews

Little Yellow Cottage New Paltz - Kitchen wash/dry

Built over 100 years ago as a chicken hatchery, this gorgeous little gem has been fully restored as a two-story guest cottage. Located in New Paltz just minutes off Exit 18 on I-87 in a very private, quiet, country setting. Only ten minutes from New Paltz Village & SUNY New Paltz and set back on a lightly traveled road for those long summer strolls. You don't even need a car to get here! It's just 12 minutes by taxi from the New Paltz Bus Station or bring your bike up and cycle everywhere!

Guest favourite
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, 370 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

Guest favourite
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, 225 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.

Guest favourite
A modern kitchen area is presented with open wooden shelves displaying dishes, glassware, and decorative items. Below, a gas stove and black refrigerator are complemented by a light fixture and a collection of utensils, offering a functional and organized space.
Cottage in Goshen
4.92 out of 5 average rating, 355 reviews

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Picture this... You escape to a relaxing, picturesque, and peaceful country cottage and enjoy some of your favorite convenience amenities like 1 Gig Wifi and your favorite streaming sources. Just 10 minutes to LEGOLAND, 3 miles to the famous Orange Heritage Trail, and less than 20 minutes to America's oldest winery, Brotherhood, this cottage has something to offer for everyone. You'll be minutes from conveniences like Target but taking in the views, you'd never know it.

Top Guest favourite
A serene lakeside view is captured at dusk, showcasing vibrant hues of orange and purple in the sky above a calm water surface. Silhouettes of trees and lanterns frame the scene, offering a peaceful ambiance as the last light fades.
Cottage in Newburgh
4.88 out of 5 average rating, 237 reviews

Cozy Lake Cottage

Cozy cottage in residential lake community, adjacent to historic fine dining restaurant. There is an approximate 150 yard walk down to the lake to enjoy the spectacular sunsets . Centrally located in the Hudson Valley near everything there is to experience. Located in our area Many Local Wineries ( Angry Orchard) Woodbury Commons Outlet Mall Historic Newburgh and Waterfront Culinary Institute of America US Military Academy New Paltz and Mohonk Mountain House

Top Guest favourite
The living room features two comfortable white sofas adorned with red accent pillows, positioned around a wooden coffee table. Natural light floods in through multiple windows, illuminating the space. A decorative flower arrangement sits on the table, enhancing the cozy ambiance.
Cottage in New Paltz
4.99 out of 5 average rating, 577 reviews

Stone House 1807. Comfort, Peace and Nature.

Historic 200 yr old stone cottage, on three floors, renovated to a high standard, creating a very comfortable and peaceful retreat, whilst retaining soul and character. Extreme cleanliness is a priority. Quality bedding assures a good nights sleep. The bathroom offers a rain shower and soaking tub. The kitchen is fully equipped and fresh produce is available from the neighboring organic farm in season. Good hiking trails are accessible from the house.

Top Guest favourite
The interior space features a high vaulted ceiling with skylights, allowing ample natural light. A stone fireplace serves as a focal point, complemented by a comfortable seating area. A wooden dining table and a kitchen island with a butcher block top are also present.
Cottage in Pawling
4.99 out of 5 average rating, 160 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 favourite
Cottage in Godeffroy
4.99 out of 5 average rating, 134 reviews

Lakefront House w/Private Dock, Fire Pit & Hot Tub

Cozy and recently renovated 1940s lakefront house right on the water. Perfect for a couple or a small family, with a king bed and a queen sofa bed. Enjoy views of the lake all around the house. Private dock, fire pit, and cedar hot tub. Under 2 hours from NYC, and 20 minutes to nearby shopping and restaurants as well as great hiking trails. High speed Internet and TV provided.

Guest favourite
A light-filled corner of the cottage features a wooden dining table with orange metal legs and two chairs. A vase of fresh flowers sits on the table, and sunlight streams in through nearby windows, illuminating the simple decor.
Cottage in Saugerties
4.95 out of 5 average rating, 260 reviews

Blue Mountain Cottage

Enjoy the best of the Catskills from Blue Mountain Cottage. The cottage is 5 minutes from many mountain trails, 12 minutes to Woodstock, 10 to Saugerties, under 30 to Hunter Mountain and 20 to Kingston. This area has so much to offer in all four seasons! We are just down the road from Indian Head Wilderness in Catskill Park, and very close to Kaaterskill Wild Forest.

Popular amenities for Bear Mountain cottage rentals

  1. Airbnb
  2. United States
  3. New York
  4. Orange County
  5. Highlands
  6. Bear Mountain
  7. Cottage rentals