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, 113 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!

Guest favorite

The exterior of Highland House is depicted, featuring a wooden deck with potted flowers and outdoor seating. Large windows allow natural light to fill the space, and solar panels are visible on the roof. The landscape in the background offers a view of open fields.

Tiny home in Mount Pleasant

4.97 out of 5 average rating, 325 reviews

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.

Top guest favorite

The living area features a cozy seating arrangement with a curved sofa and armchair, arranged around a stone fireplace. A wooden table with chairs sits nearby, illuminated by natural light streaming through the large windows, which offer views of the surrounding landscape.

Cabin in Champion

4.99 out of 5 average rating, 184 reviews

Private 1 bedroom cabin on 14 acres

Beautiful cabin in the Laurel Highlands minutes away from 3 ski resorts and many miles of trails through state forest land. Tons of local trout fishing streams. Spectacular mountain view from picture windows on either side of wood burning fireplace and from outside firepit. Cabin is situated on 14 partially wooded, partially open acres. Views of woods, mountains, and wildlife from all windows. Short drive to a number of tourist attractions, including Idlewild, OhioPyle, and Ft. Ligonier

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, 188 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, 148 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, 234 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 log cabin features a classic two-story structure with wooden siding, surrounded by vibrant autumn foliage. Soft lighting illuminates the porch, creating a welcoming ambiance. A spacious deck with railings offers an inviting space for outdoor relaxation amidst the colorful landscape.

Cabin in Normalville

4.99 out of 5 average rating, 101 reviews

Large Rustic Log Cabin in the Laurel Highlands

This cozy log cabin is conveniently located near Seven Springs, Hidden Valley, Ohiopyle State Park & Fallingwater. The log cabin is situated on a quiet lane along Poplar Run. Features: 3 bedrooms, 2 bathrooms, spacious living room, large kitchen, deck, outdoor seating, fire pit, pond. Guest house available April - Oct for additional fee. Inquire if interested. It features a queen bed, kitchenette & 1 bathroom. We offer Netflix & WiFi | NO Cable Dogs allowed for a $75.00 fee

Superhost

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

4.93 out of 5 average rating, 211 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, 188 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

4.92 out of 5 average rating, 288 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.

Top guest favorite

An outdoor seating area is furnished with multiple tables and chairs, shaded by a large umbrella. Surrounding the space are vibrant flower pots and a covered deck that extends from the home. The exterior features a blue facade and a modern metal roof.

Cabin in Farmington

4.99 out of 5 average rating, 200 reviews

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 Amphitheater, 6 mi to Ohiopyle, .2 mi Braddock’s, .3 mi Stone House Restaurant. Adults only and no pets please.

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, 202 reviews

Charming Farmhouse Apartment with Gorgeous View

Relax in this clean, comfortable, and spacious apartment. 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 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.