Vacation rentals in Chestnut Ridge

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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, 107 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

Home in Connellsville

4.95 out of 5 average rating, 180 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, 145 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 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, 230 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.

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, 182 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 favorite

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

4.94 out of 5 average rating, 282 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 favorite

A charming cabin is positioned among tall trees, featuring a white exterior and a dark roof. A gravel pathway leads to the entrance, and additional cabins are visible in the background, surrounded by a natural setting.

Cabin in Uniontown

4.88 out of 5 average rating, 32 reviews

Cozy cabin /tiny house in country setting.

6 cozy cabins at the foot of the Allegheny Mountains. Close to many historical and recreational sites. Perfect for a family event. . Relax with the whole family at this peaceful place to stay. Wi-Fi is very spotty. The ladder to the loft is steep. There is no privacy between the loft and the main floor. No smoking ( includes vapes and marijuana) of any kind. Smoking is allowed at fire pits and pavilion. There is a $250.00 fine.

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

4.98 out of 5 average rating, 50 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, 45 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.

Top guest favorite

The exterior of a spacious farmhouse apartment is displayed, featuring a large structure with multiple windows and dormer roofs. A covered front porch is lined with decorative plants, while a flag pole stands beside the entrance. Lush greenery surrounds the home.

Guest suite in Morgantown

5 out of 5 average rating, 192 reviews

Charming Farmhouse Suite • Peaceful & Private

We love surprising our guests by being even better than the photos. Our goal is to delight you—making your stay feel spotless, peaceful, and worth more than you paid. With thoughtful, unlisted touches and no checkout chores, we aim to make your visit effortless. This clean, comfy, and spacious farmhouse apartment has a living room, kitchenette, bedroom, and large bath.

Top guest favorite

A cozy living area features a comfortable sofa with decorative pillows, paired with a stylish armchair. A coffee table and a television stand enhance the space, while double French doors open to a view of the outdoors. Natural light floods the room through the blue curtains.

Apartment in Morgantown

4.98 out of 5 average rating, 102 reviews

Creekside Condo

Located close to both hospitals, stadiums, and popular dining options. Quiet, ground level, Creekside condo. We encourage in stay communication to ensure the best stay possible. The deck is on the smaller side - It’s a 4x8 space on the backside of the building facing a creek. In the summer and fall it provides a quiet and peaceful place for coffee and relaxing.