Family-friendly holiday rentals in Canonsburg

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.

Groovy Retro Get-Away

With a retro flare & a mid-century modern vibe, you'll enjoy this quaint bungalow in a quiet residential neighborhood conveniently located minutes from downtown Pittsburgh, the airport, many great sites, must-see attractions, universities & colleges. Whether you're in town for business, a sports event, bringing a student back to school or just want some time away, this cozy space is perfect! Everything in this bungalow is well appointed including keurig coffee, WiFi & a smart TV for streaming.

"The Cottage on Summit"

The "Cottage on Summit" is charming & updated Historical 1932 Cape Cod, located in the beautiful Bethel Park community. Relax with the whole family in our peaceful, cozy yet spacious home, boasting privacy, comfort and safety, nestled within the Summit neighborhood . NOTE: A "request to book" will need additional information prior to "confirming by the host". Verified ID and at least ONE Positive review & No Negative reviews from previous stays are needed. House rules strictly enforced.

Head to Pittsburgh From Mt. Lebanon Cottage

Mt. Lebanon Cottage is a craftsman-style home that fuses contemporary styles with traditional elements. Enjoy our well-equipped kitchen, enjoy a coffee for two on the deck nestled in the trees or unwind on the front porch and enjoy the friendly neighborhood vibe. The home is in a walkable neighborhood of tree-lined streets and friendly locals. Blocks from unique shopping boutique options and dine at tasty local restaurants. Hike in the nearby nature and visit Pittsburgh just minutes away.

Cozy Bright Mt. Leb Cottage | 2 m to T to Stadiums

Relax with the whole family at this peaceful place to call your own. This lovely 3 bedroom cottage welcomes you and your guests in a private setting. This home has been updated and is a perfect place to feel right at home whether you are visiting family and friends or here on a business trip. Everything is here for you, from kitchen items, toiletries, washer and dryer and plenty of great outdoor areas to finish your evening on a great note. Lovely children's park down the street as well.

Seneca Place: A historic home in Mount Lebanon.

Seneca Place is a historic home. Our guests have the best of both worlds: a private full residence with attentive and available hosts (right next door). Please note that we charge by guest for requests over two, so please enter the correct number of guests to fully understand your costs. This neighborhood is very quiet with little to no traffic and the hosts are ten feet away. There is a covered side patio with an outdoor sofa as well as a connecting back patio with a fire pit.

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.

Brush Run Cottage

A comfortable private lower level (no stairs) apartment in the lower level of our home. We are in a country setting near interstate 79. Casual decor in a private space. Attractions 10-25 minutes of this location include: Key Bank Pavilion, Montour Trail, Southpointe Business Park, Southpointe Golf Club, dining, Meadows Racetrack and Casino, Tanger Outlets, Cemetery of the Alleghenies, Washington & Jefferson College as well as all of the attractions downtown Pittsburgh has to offer.

Spacious 2 Bedroom in a Convenient Location

Our property is located right off I-79 in Bridgeville, Pa. The home is completely remodeled and features a renovated kitchen with all new appliances, 55" & 65" flat screen televisions, a well lit off-street parking area (5 cars), and is in walking distance to the business district with restaurants, bars, cafes and shops. 2 bedrooms: 1st floor bedroom (1 Queen bed) with 1 full bath, 2nd floor bedroom (1 Queen bed) and 1 full bath. Large laundry area with washer and dryer.

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.

Southern Pines Lodge-Unique & Charming

Come enjoy a relaxing stay at this unique & cozy home for a getaway, retreat, family or business related trip. The listing is for 6 people but able to host up to 15 guests but there will be an additional $30 per person after the first 6 guests. You will find yourselves close to The Meadows Racetrack & Casino, Tanger Outlets and a 5 minute walk to all different types of eateries/restaurants. In addition, it's only 25 minute drive to downtown Pittsburgh.

Secluded Tiny “Ginseng House” Artist Retreat

"Ginseng House" - Our premiere off-grid tiny house! A hand-crafted work of art using our own sawmill lumber. Beautiful wooded setting surrounded by 180 acres of private land and two miles of beautiful Buffalo Creek frontage to enjoy. One very comfortable queen bed in the loft and a fold out double bed love seat on the main floor. Extra guests may pitch tents for $10/night/person. Pets welcome - $35/pet - see pet policy.