Holiday 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!

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.

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.

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.

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.

Charming 1850s River front home

Step back in time in this lovingly restored Victorian home, nestled along the scenic Monongahela River in historic Greensboro, PA. Built in the 1850s, this enchanting retreat offers the perfect blend of timeless character and cozy amenities — including a fireplace in every room. The home features two bedrooms, two full baths, and a bonus loft. Whether you're watching the sun rise over the water, fishing the Mon, or enjoying a staycation, this riverfront gem offers a peaceful getaway.

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.

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.

Cozy Cabin/tiny house in country Setting.

Cabins set at the foot of the Allegheny Mountains and close to many historical and recreational site. 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.

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.