
Holiday houses in Chestnut Ridge
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Top-rated holiday rentals in Chestnut Ridge
Guests agree: these stays are highly rated for location, cleanliness and more.

Large Lodge in the Laurel highlands
Large Lodge on 3 acres w/ beautiful Stream Running through the woods. This Lodge is perfect for a relaxing mountain vacation. Large enough for the whole family to spread out & have fun. Snuggle up by the fireplace, enjoy a game of pool, head outside, relax in the hot tub, or go fishing! This place has got something for everyone. It’s right off Rt. 40. Minutes from Nemacolin, Ohiopyle, Fort Necessity & plenty of restaurants nearby. 3beds 2 baths (2 queen 1 full) 1 sleeper sofa. Grill Rental $25

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!

Bird's Eye View
Nestled high amidst the sturdy branches, "Bird's Eye View" is a sanctuary suspended between earth and sky. Located less than 5 minutes from Deep Creek Lake and perched among the foliage, our treehouse offers a panoramic perspective of the surrounding forest, granting its visitors an unparalleled vantage point to observe nature's wonders. Relax in the hot tub and take in an amazing sunset. The home is a harmonious blend of locally-crafted art and furniture to add rustic charm and modern comfort.

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.

Ohiopyle Luxury Treehouse
Come unwind in our one-of-a-kind Treehouse getaway just minutes from Frank Lloyd Wright’s Fallingwater and Ohiopyle! Located more than 1/4 Mile off the county road, you will only hear the birds chirping as you sit on the covered patios taking in the beauty of the surrounding hardwoods and ferns. Enjoy a morning hike on our mile long private hiking trail that will take you across a clear mountain stream, into the canopies of the mountain laurels and through a rock boulder field. Sorry NO PETS.

Coffee by the Fire+Stars at Night- Vintage Suite
Stay in our elegant Vintage-Modern Home Only 20min from Fallingwater. ✔Queen Beds+Organic bedding, cleaned w/ natural cleaners for your BEST rest w/o combatting toxins/fragrances ✔Ideal for Families and Staycations ✔Inviting Dining and fully stocked Kitchen ✔Fast WIFI+Netflix ✔Off-Street Parking ✔Self check-ins with secure keypad ✔Washer/dryer ✔Free breakfast Everything you need is provided - Just pack up your clothes and enjoy your stay with us! Book today to reserve our luxury home!

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.

Sunbeams Cottage
Small home is completely remodeled using traditional woodwork craftsmanship for a warm feel. Full appliances and amenities are supplied in the cottage. Evening and breakfast snacks included. Tasty public tap water for drinking and cooking. Private lane leads to the home with a spacious covered porch overlooking hillside and field. Ideal location at foothills of Laurel Highlands and outskirts of Pittsburgh. Town of Mt. Pleasant is just minutes away providing restaurants and shopping.

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.

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.

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.
Popular amenities for Chestnut Ridge holiday rentals
Other great holiday rentals in Chestnut Ridge

Rustic Luxe Cabin (4x4 Required)

The Dave Cave

Cozy 3bd, 2bath for family vacation/hiking/getaway

Buffalo Bill's "The Silence of the Lambs" House

Shipp's Creek: Luxury Creekside Container Retreat

Cozy Cabin | 15 Min to Ski & Ohiopyle Trails

Situated at the foot of the Laurel Highlands.

Cozy upstairs apartment!
Destinations to explore
- Norfolk Holiday rentals
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- Greater Toronto Area Holiday rentals
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- PNC Park
- Carnegie Mellon University
- Wisp Resort
- Fallingwater
- Seven Springs Mountain Resort
- David Lawrence Convention Center
- Acrisure Stadium
- Pittsburgh Zoo & PPG Aquarium
- University Of Pittsburgh
- Idlewild & SoakZone
- Ohiopyle State Park
- Raccoon Creek State Park
- Point State Park
- Kennywood
- Sri Venkateswara Temple
- National Aviary
- Phipps Conservatory and Botanical Gardens
- Schenley Park
- Stage AE
- Petersen Events Center
- Children's Museum of Pittsburgh
- Cathedral of Learning
- Carnegie Museum of Art
- Senator John Heinz History Center





