Holiday houses in Chestnut Ridge

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chestnut Ridge

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost
Home in Grindstone
5 out of 5 average rating, 3 reviews

The Coal Patch Cottage

Enjoy your stay in the rolling foothills of Western Pennsylvania with this full house rental. This 1920 duplex has been completely renovated as a single family home. It is located in the historic Rowe’s Run Coal Mine Patch where the original company store still stands. There is no shortage of fun, located within an hour of Pittsburgh, Seven Springs Ski Resort, Nemacolin Resort and Casino, Frank Lloyd Wright’s Falling Water, Ohiopyle State Park, Fort Necessity National Park and Morgantown, WV.

Guest favourite
A charming two-story yellow house is displayed with a welcoming porch and landscaped yard. A cyclist rides along the street, showcasing the convenience of the nearby bike trail. A white picket fence provides a boundary, and colorful flowers enhance the outdoor setting.
Home in Connellsville
4.95 out of 5 average rating, 151 reviews

Trailblazer's Haven

Our cozy Airbnb, located on the bike trail between Pittsburgh and Washington DC, offers three comfortable bedrooms, a kitchen with all the amenities, and a comfortable living area. It's an ideal home base for exploring nearby attractions such as Ohiopyle, Seven Springs, and Fallingwater. In addition to its convenient location, our property provides a peaceful retreat from the hustle and bustle of everyday life. Please book your stay with us today and experience the natural beauty of the area!

Guest favourite
The elevated house features a spacious porch, supported by sturdy posts, offering a view of the surrounding greenery. A large flowering shrub adds color to the landscape, while a small, neatly trimmed bush provides depth to the scene.
Home in Perryopolis
4.84 out of 5 average rating, 297 reviews

132 Wickhaven-Deer Path Lane Guesthouse

If you enjoy privacy and pretty scenery this is the place for you. Enjoy nature and the sounds of waterfalls from the elevated deck. This two bedroom house is all by itself with an updated kitchen. Just a short drive to Laurel Caverns, Falling Water and Ohiopyle. There is plenty of firewood on site for campfires. The long driveway is dirt and gravel and rough and you have to ford a small stream. You don’t need a 4 wheel drive but you do need a vehicle with clearance. Pickup or SUV recommended.

Top Guest favourite
A private deck is shown, furnished with two red chairs, overlooking a tranquil landscape. The sky is filled with soft hues of orange and purple from a sunset, while trees are silhouetted against the colorful backdrop.
Apartment in Perryopolis
4.99 out of 5 average rating, 165 reviews

Relaxing River View Apt near MM103 of GAP trail

Enjoy a river view escape with direct access to the Greater Allegheny Passage (GAP) Bicycle Trail, and the Youghiogheny River in the quaint town of Perryopolis, PA, just 31 miles south of Pittsburgh. All new modern apartment. Bike 50 miles into, or from, Pittsburgh with stops along the way to shop and eat. Very close to both Winslow and Visnoski Wineries which often have outdoor music and concerts! Or spend the afternoon, relaxing on the deck. Restaurants and groceries available in town.

Top Guest favourite
The kitchen features a retro design with vibrant yellow walls and patterned curtains. A vintage refrigerator is positioned beside a compact dining table surrounded by four yellow chairs. A gas stove and a window bring natural light into the space, showcasing a lively, nostalgic atmosphere.
Home in Belle Vernon
4.98 out of 5 average rating, 132 reviews

Relax & Revisit Yesterday with a Retro Staycation!

Relax during your stay in a home where the 1950s, 60s & 70s come alive. This restored former family home is filled with authentic treasures that bring you back to the decades of America's past. Enjoy the Nifty 50s Kitchen, an art deco 1940s Dining Room, a living room in 'mod' 1960s decor, retro 70s bedrooms, full basement with a custom 1950s Knotty Pine bar, a record player, along with vintage Pinball machines. Experience a step back in time as you remember fondly your Good Ol' Days.

Guest favourite
Treehouse in McHenry
4.96 out of 5 average rating, 141 reviews

Treehouse in Deep Creek Lake

Newly built, Whispering Woods is a custom-made treehouse surrounded by stunning scenery just minutes from Deep Creek Lake and Wisp Resort. No detail was overlooked in the spacious interior that includes 2 bedrooms, 2 baths, a fully equipped kitchen, and a sitting area with a 65” TV. The amazing outdoor living space includes expansive decks, a fire pit, and a bubbling hot tub. For a unique and memorable experience from start to finish, come relax and reconnect at this treetop escape.

Top Guest favourite
The mobile home is set in a grassy area, displaying a simple exterior with large windows. A wooden porch leads to the entrance, surrounded by spacious lawn and trees. The structure is designed to blend with the serene landscape.
Guesthouse in Connellsville
5 out of 5 average rating, 125 reviews

Peggy's Guest Hideaway

A very quiet and peaceful mobile home / guest house located in Connellsville Pennsylvania. We are close to many popular sites such as the Great Allegheny Passage bike trail and the Laurel Highlands. If you are looking for a place to unwind or just a place to get away for awhile and do not care for hotels or people drama at the end of the day then this place is a good fit. In the evenings the crickets are the loudest noise in the air and many mornings there is deer in the yard.

Top Guest favourite
An outdoor seating area is furnished with multiple tables and chairs, shaded by a large umbrella. Surrounding the space are vibrant flower pots and a covered deck that extends from the home. The exterior features a blue facade and a modern metal roof.
Cabin in Farmington
4.99 out of 5 average rating, 229 reviews

Mountain Clay Hideaway Couple’s Retreat w/ Hot Tub

Take it easy at this unique and tranquil getaway. Adventure all day or simply relax, rejuvenate and reconnect with your special someone. Enjoy the hot tub under the mountain stars. Customize your stay with a variety of additions. Conveniently located near all of the best the area has to offer! 700 ft to Timber Rock, 6 mi to Ohiopyle, 8.8 mi Fallingwater, .2 mi Braddock’s, .3 mi Stone House Restaurant. Adults only and no animals please. This is a hypoallergenic home.

Top Guest favourite
A cozy cottage is nestled among trees, featuring a spacious deck with chairs and a grill. A picnic table is situated on the lawn, providing ample outdoor seating. The surrounding greenery enhances the private and serene atmosphere of the property.
Cottage in Normalville
4.94 out of 5 average rating, 592 reviews

Nice and Cozy Rental

Great cottage nestled in the mountains on 63 wooded acres with barn, spring house and main house. Cottage has fireplace with first ring of logs provided. Two Smart TVs , VCR and DVD player with tapes and DVDs provided. Large deck and patio furniture off the living room with private woodland views and a babbling brook. Outdoor fire pit also provided. Close to Fallingwater, Ohiopyle and Seven Springs. Pet friendly (up to 2) and beautiful hiking trails in our woods.

Top Guest favourite
The Hobbit House features a unique multi-level design with a grassy roof and vibrant red doors. A pathway leads to the front, flanked by lush greenery and stone accents, while a decorative wheel is positioned near the entrance, adding to the charming exterior.
Cabin in Farmington
4.99 out of 5 average rating, 228 reviews

Ohiopyle Hobbit House

One of a kind Lord of The Rings themed Hobbit House. With hidden surprises around every turn. You won't be able to stop uncovering the small details that will add to your enjoyment of your stay. Almost everything in the house was custom made by the builder to add to the unique charm of the house. From the medieval doors with operable speak easy look throughs and the whiskey barrel cabinets, you don't want to miss putting this house on your travel bucket list.

Guest favourite
The living area features a comfortable couch and armchair set near a stone fireplace. Large windows allow natural light to fill the space, offering views of surrounding greenery. A dining table is positioned nearby beneath exposed beams and a ceiling fan.
Chalet in Acme
4.93 out of 5 average rating, 334 reviews

Secluded Chalet near Ohiopyle and Seven Springs

Leave the bustle behind for the whispering oaks and calming embrace of our renovated Laurel Highlands chalet. Enjoy grilling on the deck, sitting around the fire ring, watching wildlife in the woods, or reconnecting with friends and family inside the cozy chalet. Shrouded by towering oak trees, the chalet is quiet and feels secluded. Yet, it’s only minutes away from Ohiopyle, Seven Springs, Fallingwater, and other popular attractions in the Laurel Highlands.

Guest favourite
Shipping container in Acme
4.88 out of 5 average rating, 305 reviews

The Laurel Haven Container

Experience the soothing sounds of nature during your stay in the Laurel Haven Container. Designed for relaxation and reconnecting with the outdoors, this lakeside retreat offers a peaceful escape like no other. Firewood bundles are available on-site for a small fee, perfect for enjoying the fireplace or a lakeside fire pit. Nestled in the heart of Pennsylvania’s Laurel Highlands, it’s the only container home of its kind in the region!

Popular amenities for Chestnut Ridge holiday rentals