
Vacation rentals in Chestnut Ridge
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Chestnut Ridge
Guests agree: these stays are highly rated for location, cleanliness, and more.

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!

Tiny House - Big Farm Adventure near Pittsburgh
Enjoy an Adventure in "Glamping" at Highland House on Pittsburgher Highland Farm. This custom built Tiny House is situated on over 100 acres of rolling farmland, hills and forests, with Scottish Highland cattle, chickens, sheep & lambs, pigs, fish in the pond, and 2 beehives. You have use of the entire farm during your stay. Located about 45 minutes south-east of Pittsburgh in Pennsylvania's beautiful Laurel Highlands, there is lots to see and do both on site and nearby. Photos current 2024.

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.

Coopers Rock Retreat
Industrial farmhouse studio apartment nestled in the hills of West Virginia. Located just 15 minutes to downtown Morgantown and only 5 short minutes away from Coopers Rock State Forest. Spectacular landscape views from dusk to dawn and breathtaking star gazing on clear nights. Guests have their own private entrance to come and go as they please, a full kitchenette to make home cooked meals while on the road, large bathroom with walk-in shower, queen size bed, and an extra long single futon.

Vintage Vogue Suite, Patio *Fire Pit* Grill +WI-FI
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.

Mid century modern getaway cottage near Ohiopyle
Welcome to Humming Bird Haven, tucked away in the Laurel Highlands just minutes from Ohiopyle. Enjoy this getaway property that has an updated kitchen with a beautiful live edge dining table. Use this cottage as a base to enjoy the many activities the area has to offer or just relax on the large open porch. A small creek runs through the property with a fire pit area and a large hammock to bird watch in. We are nestled in between a small farm and an old junk yard filled with rusty cars.

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.

Newly renovated 3BR on 1 acre!
YOUR HOME AWAY FROM HOME!! Relax with friends and family at this peaceful place to stay. Right down the road from cheat lake and multiple golf courses. 15 minutes from WVU and Mountaineer Field. 65 inch big screen TVs in the living room and master bedroom. 50 inch TV in the other room with a queen bed. Bunk beds twin over full with trundle bed underneath. Outdoor gas fireplace on deck. Large BBQ grille. 15 minutes to Coopers Rock. 12 Minutes to Fright Farm. 3 miles from Cheat Lake Park.

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.

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.

Quiet Apartment close to Town Center
A private and quiet stay await you at The Holler, our 1 Bedroom, open concept, budget friendly apartment. The unit boasts about 800 sqft of newly renovated space, complete with all the amenities you would need for a quick stay or something longer term. Secluded at the end of a dead end road, The Holler offers an acre of open land to stretch out for you or your dog. 10 Minutes to either hospital or the interstate, perfect for those traveling for work.
Popular amenities for Chestnut Ridge vacation rentals
Other great vacation rentals in Chestnut Ridge

Welcome to The Cowboy Castle!

Brickyard Hill Farmhouse

The Half Glass

The Lily Pad Cabin

Private Mt Lebanon Retreat Near Airport/Downtown

Beats-A-Hotel

Luxury Schoolhouse Loft

The birdhouse
Destinations to explore
- Greater Toronto and Hamilton Area Vacation rentals
- Greater Toronto Area Vacation rentals
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- South Jersey Vacation rentals
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- Wisp Resort
- PNC Park
- Carnegie Mellon University
- Strip District
- Fallingwater
- Seven Springs Mountain Resort
- Pittsburgh Zoo & PPG Aquarium
- Idlewild & SoakZone
- National Aviary
- Kennywood
- Raccoon Creek State Park
- Point State Park
- Ohiopyle State Park
- Phipps Conservatory and Botanical Gardens
- Carnegie Museum of Art
- PPG Paints Arena
- Schenley Park
- Children's Museum of Pittsburgh
- Laurel Mountain Ski Resort
- Senator John Heinz History Center
- Randyland
- Cathedral of Learning
- West Virginia University
- Carnegie Science Center




