Vacation rentals in Chestnut Ridge

Uniontown Cottage with breakfast & on-site winery

Welcome to your home away from home at Deer Creek Winery! Nestled in the heart of Pennsylvania wine country, our cottage on the Watson Estate offers a unique bed and breakfast experience with FREE wine tasting! This rustic cottage with front porches and rocking chairs overlooks peaceful woods, fields, and pastures - the perfect setting for a serene and private getaway. Inside, you'll find an open living space with a king bed, mini-kitchen, smart TV, bathroom, and climate control. Pets allowed

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.

Welcome to The Cowboy Castle!

Welcome to THE COWBOY CASTLE! A spacious, unique home with skylights, a peaceful waterfall, and farm views with livestock right in the backyard! LOCATION! Only 1.5 miles from Uniontown’s major shopping & dining. 16 miles to Ohiopyle State Park, Falling Water, Fort Necessity, & Lady Luck Casino. 3 miles from The Grayson House Wedding Venue - perfect for wedding weekends or a bridal suite! 20 miles from WVU & Cheat Lake - ideal for graduation, games, college events, lake activities & eateries!

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.

Large Lodge in the Laurel highlands

Large Lodge settled on 3 acres w/ a 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.

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.

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

Our Guest Home

*****THIS HOME IS NOT SHARED***** Relax with the whole family at this peaceful country home, located 20 minutes from Pittsburgh, central to various parks, eateries, shopping areas & 3 casinos (each 19 miles away) 1.5 miles off route 51. Located on a private lane with plenty of room to park, trucks, campers & atvs welcome. The home also has an animal/dog outside enclosure so your furry friends can play outside! (This is a shared dog yard from time to time with our golden doodles)

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.

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.