
Holiday houses in Chestnut Ridge
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Top-rated holiday rentals in Chestnut Ridge
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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.

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!

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.

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.

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.

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.

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.

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.

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.

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.

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.

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
Other great holiday rentals in Chestnut Ridge

Highland Hideaway

Rustic Luxe Cabin (4x4 Required)

Diamond View PA: A-Frame~Hot Tub~Sauna~City View

Uniontown Cottage with breakfast & on-site winery

Brickyard Hill Farmhouse

FLW Inspired Home--close to NWL and Fallingwater!

Shipp's Creek: Luxury Creekside Container Retreat

Cozy Cabin | 15 Min to Ski & Ohiopyle Trails
Destinations to explore
- Philadelphia Holiday rentals
- Washington Holiday rentals
- Columbus Holiday rentals
- Pittsburgh Holiday rentals
- Ocean City Holiday rentals
- Cleveland Holiday rentals
- Virginia Beach Holiday rentals
- Cincinnati Holiday rentals
- Raleigh Holiday rentals
- Detroit Holiday rentals
- Niagara Falls Holiday rentals
- Mississauga Holiday rentals
- PNC Park
- Acrisure Stadium
- Carnegie Mellon University
- Fallingwater
- Wisp Resort
- Seven Springs Mountain Resort
- University Of Pittsburgh
- David Lawrence Convention Center
- Pittsburgh Zoo & PPG Aquarium
- Ohiopyle State Park
- Idlewild & SoakZone
- Sri Venkateswara Temple
- Raccoon Creek State Park
- Point State Park
- Stage AE
- Petersen Events Center
- Phipps Conservatory and Botanical Gardens
- Kennywood
- Schenley Park
- National Aviary
- Carnegie Science Center
- West Virginia University
- Deep Creek Lake State Park
- Swallow Falls State Park





