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.

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Top guest favorite

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

4.97 out of 5 average rating, 104 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!

Superhost

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, 289 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 favorite

An inviting entrance showcases a well-lit doorway framed by a wooden accent. Pebble-strewn pathways lead to the entrance, complemented by potted plants that add greenery. A wooden fence partially encloses the area, offering privacy while enhancing the modern aesthetic of the home.

Home in Connellsville

4.95 out of 5 average rating, 176 reviews

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!

Top guest favorite

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, 143 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.

Guest favorite

A bright living area features a mix of textured seating with a red and yellow sofa, accompanied by a coffee table. High ceilings accentuate the space, with a brick column and skylights above. A television sits adjacent to a kitchen area with wooden cabinets and bar seating.

Cottage in Dunbar

4.91 out of 5 average rating, 180 reviews

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.

Top guest favorite

An open interior space showcases rich wooden walls and a vaulted ceiling with warm lighting. A dining table, set for meals, is positioned near a window. The kitchen area is visible, equipped with modern appliances, and the entrance features a rustic wooden door.

Cottage in Mount Pleasant

5 out of 5 average rating, 227 reviews

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.

Guest favorite

The exterior of a two-story house features a sloped red roof and white siding with red shutters. A spacious porch with multiple seating areas invites relaxation, framed by well-maintained greenery including tall trees. A clear sky enhances the inviting appearance of the home.

Home in Connellsville

4.94 out of 5 average rating, 205 reviews

The River House a Waterfront paradise on the trail

Welcome to Riverside! Located directly on the Youghigheny River in Connellsville PA. We are a block from the Great Allegheny Passage Bike Trail. Newly Renovated 6 Bedroom House with all the amenities. Cast your line into the river from the back yard. Drop a kayak in from the private beach area. Bike to Ohiopyle. Hike the scenic trails of the GAP. Or just enjoy a game of billiards or cornhole. In the evening relax in the hot tub or sit around the firepit with the family.

Top guest favorite

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, 180 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.

Top guest favorite

A cozy seating area is featured with a gray two-person sofa adorned with patterned cushions. A dark coffee table sits in front of the sofa, which is placed on a decorative area rug. Soft light is emitted from a nearby lamp, illuminating the space.

Apartment in Monongahela

5 out of 5 average rating, 46 reviews

Charming Loft in Historic Town

This is a newly renovated loft apartment above the garage in a quiet older established neighborhood with treelined streets and beautiful well kept historic homes in Monongahela, PA. Close access to Routes 43, 70, 51 and interstate 79. This rental provides access to the greater Pittsburgh area and the larger cities of Uniontown, Greensburg and Washington areas. All of these areas are within 25 miles of the property.

Guest favorite

A spacious room features a large bed and a desk with a chair. Two sets of glass doors provide access to a deck with river views. Comfortable seating options are present, and soft tones create a calming ambiance, inviting relaxation.

Apartment in Coal Center

4.98 out of 5 average rating, 43 reviews

Riverview Suites

Discover the serene charm of our private riverfront rooms, thoughtfully nestled near the picturesque Pennwest University. Our “One Bedroom Luxe Suite” offers a unique blend of comfort and convenience. Private off street parking and gated privacy for your relaxation. Embrace nature as you gaze upon the mesmerizing river views from our expansive connecting deck and inviting gazebo.

Superhost

The exterior of the container home is surrounded by lush greenery, showcasing a front deck with wooden railings and cozy seating. Large windows provide natural light, creating a connection with the outdoor landscape. A pathway leads up to the welcoming entrance.

Shipping container in Acme

4.89 out of 5 average rating, 238 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. Nestled in the heart of Pennsylvania’s Laurel Highlands, it’s the only container home of its kind in the region!

Top guest favorite

A spacious bedroom features a large bed with neatly arranged grey and white linens. Two bedside tables with lamps flank the bed, and decorative wall art is displayed above. Soft lighting enhances the serene atmosphere of the room.

Guest suite in Morgantown

5 out of 5 average rating, 185 reviews

Charming Farmhouse Apartment with Gorgeous View

Clean, comfy, and spacious! Relax and enjoy the beauty of nature in the comfort of a charming private farmhouse apartment. This spacious suite has a separate living room, kitchenette, and bedroom plus a large bathroom. Quiet and serene, the word our guests repeatedly use to describe it is "peaceful".