Holiday rentals in Smithton

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.

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.

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.

Railside Inn - Vintage Home Built in 1900

Located in West Newton,PA enjoy what this 3-bedroom house has to offer. The bedrooms include a king bed, and six twin beds, providing comfortable sleeping options for guests. With two bathrooms, everyone can enjoy plenty of privacy and convenience. A pleasant living room features a sofa bed and a child bed, perfect for relaxing or extra guests. This fantastic house creates a tremendous space for families or groups looking to unwind. Book now and enjoy everything this house has to offer.

Cozy Cabin | 15 Min to Ski & Ohiopyle Trails

Unwind at Underwood Outpost, a cozy cabin tucked in the woods of Fayette County, PA, just 15 minutes to both Seven Springs Resort and Ohiopyle State Park. Whether you’re here for a romantic escape, a family retreat, or an adventure with friends, this cabin blends rustic charm with modern amenities. Relax by the firepit, sip coffee on the porch surrounded by trees, and the sound of a running creek, or explore year-round activities — from hiking and kayaking to skiing nearby in winter.

Relax & Revisit Yesterday with a Retro Staycation!

Relax during your stay in a home where the 1950s, 60s & 70s come alive. This restored former family home is filled with authentic treasures that bring you back to the decades of America's past. Enjoy the Nifty 50s Kitchen, an art deco 1940s Dining Room, a living room in 'mod' 1960s decor, retro 70s bedrooms, full basement with a custom 1950s Knotty Pine bar, a record player, along with vintage Pinball machines. Experience a step back in time as you remember fondly your Good Ol' Days.

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.

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 142 acres of rolling farmland, hills and forests, with Scottish Highland cattle, chickens, sheep & lambs, pigs, beehives and much more. 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 updated 2026.

GAP Trail | Bike, Hike, Explore | Near Pittsburgh

All season cottage just a short walk with direct access to the Boston Trailhead on the Great Allegheny Passage. At Less than 20 miles (~40 min.) southeast of downtown Pittsburgh, it's an ideal home base for GAP Trail adventurers and regional travelers seeking a peaceful off the beaten path stay. A Short drive to groceries ,coffee shop, bakery, and dining. *Contact host for 1 day stays. *Kennywood Park-11mi *Golden Triangle Bike Rental-15mi *PNC Park-17mi *Point State Park-20mi

Brickyard Hill Farmhouse

This 1860 Farmhouse is situated on 72 Acres and is located between Downtown Pittsburgh and the Laurel Mountains. Surrounded by some of the finest Bicycle Trails, Ski Resorts, Whitewater Rafting and Several Wineries. A Large Covered Deck offers peaceful viewing of Wildlife in a Country setting. Storage space for your Bicycles, Kayaks and Skis. A true Country Living experience close to activities. A great get away for Families, Guest and Couples. Near several Wedding venues.

The Lily Pad Cabin

Cozy cabin offers open floor plan with covered porch overlooking small pond on our property. Uniquely decorated. Views of woods & fields, but close to numerous restaurants, parks & walking trails, & TRAX Farms. The Trolley to Pittsburgh is two minutes away. Should you need single night accommodation, please message me for consideration. Also consider “Mojo’s Loft”, our pet-friendly rental or Jackson Hill Cabin, our full log home with three bedrooms & a pool table.

Walk to BTV Winery | Near Corporate Offices

Extended stay friendly - great for work assignments and temporary housing! Steps away! → Bella Terra Vineyards Looking for the perfect place to stay when attending a wedding or event at Bella Terra Vineyards? Look no further as we are located across the street! We are also happy to accommodate mid-term stays for traveling professionals and insurance relocations! 🐾 Pet-friendly amenities (crate, bowls, towels) 🚀 Blazing-fast WiFi (1000 mbps) 🔥 Shared Firepit Area