Holiday rentals in Shippensburg

Old Homestead - Rest, Relax and Renew

Welcome to the "Old Homestead." If you are looking for a quaint and relaxing getaway, then the Old Homestead is the perfect spot. Located between Shippensburg/Carlisle areas, there is so much to see and do within driving distance. History enthusiast...you have so many places to choose from. Maybe wine is more to your liking...it's a matter of which winery do I choose first. Enjoy hiking...then nearby Michaux State Forest is the perfect place to go or the Cumberland Rails to Trails. Perhaps you prefer to just relax and enjoy dinner on the deck or sit around a firepit and enjoy the evening. Whatever your preference, be sure to enjoy your "home away from home."

Value · Family · Kitchen

The Frame ~ Charming Nature Escape ~ Hot Tub ~ BBQ

Escape to the charming 2BR 1Bath A-frame on a secluded wooded property just 10 mins away from Shippensburg, PA. Whether you're looking to savor nature‘s tranquility from the luxurious hot tub, share stories around the fire pit, or explore picturesque Cumberland Valley, this will be the ideal starting point for your adventures. *2 Comfortable BRs *Open Design Living *Full Kitchen *Smart TV *Backyard (Hot Tub, Sauna, Fire Pit, BBQ, Outdoor shower) *High-Speed Wi-Fi *Free Parking *EV charger

Location · Value · Decor

Prince Street Suite

Freshly renovated in 2025, this suite is right in the heart of downtown Shippensburg, in a relaxed setting. It has a nice private yard bordered by greenery. It is located 1/2 mi. from Shippensburg University, and less than 40 minutes from Gettysburg. The suite is part of a larger Victorian style home that was built in 1893. It has tons of charm and a lot of nice natural lighting. There are no TV screens but we do have fast WIFI. There is 1 queen and 1 double bed in the suite.

Location · Family · Hospitality

1789 Historic Gem | Modern for 9

The Historic Doctor’s House | 1789 Retreat Step into this tastefully restored 1789 home in downtown Shippensburg! Perfect for up to 9 guests, it’s a spacious getaway for history lovers, nature explorers, and road trippers. 5 Beds | 4 Bedrooms | 3 Baths Pet-Friendly | Full Kitchen | Walk to Cafés & Shops | Movie Room w/ Projector Explore Gettysburg, Cumberland Valley, Shippensburg University, or simply unwind in this charming, historic home. Book your stay today!

Location · Family · Checkout

Spectacular views, intimate dome

Come experience a truly one of a kind polycarbonate dome tucked away in the Appalachian mountains! Situated on the mountainside overlooking the scenic Cumberland valley. Complete privacy, stunning sunsets, and amazing amenities! The dome is climate controlled. The spacious deck is equipped with a meticulously maintained hot tub, and a blackstone griddle. This offers the unique opportunity to be immersed in nature, yet enjoy numerous amenities and comfort.

Location · Value · Biking

Homestead, a serene organic farm minutes off I81.

Visit the Homestead, just a few miles off I-81 in Chambersburg. The serene landscape offers fresh air and open space. This historic home on 130 acres of farmland presents bed/bathrooms on the first and second levels and relaxing living space for all guests. Multiple work areas are equipped to offer you a desk and comfortable chair - boasting picturesque scenes. A large bright room, seating 35 attendees, is also available for hosting special events.

Location · Value · Layout

Edgewater Lodge

A perfect place to get away from the stresses of life to relax and unwind . You Can have a seat on the large porch overlooking the Conodoguinet creek and enjoy watching nature , watch your kids playing and splashing in the creek , make dinner with the BBQ grill on the back patio or be just plain lazy ! There is no tv at this place , our goal is to have our guests enjoy nature and in this way be refreshed and ready to go back to work.

Family · Value · River

Charlie’s Place-Beautiful, quiet 2-bedroom cabin.

Our cabin is located on a private stoned road. Very quiet and remote location. Keep this in mind when booking. 25 minute drive to downtown Gettysburg, 40 minutes to Carlisle Fairgrounds. Near Michaux State Forest, Pine Grove Furnace State Park and Caledonia State Park; many hiking, ATV and snow mobile trails. For those that enjoy skiing we are 30 minutes to Liberty Mountain in Fairfield and 50 minutes to Roundtop Mountain in Lewisberry.

Family · Location · Condition

The Quaint Queen

Welcome to the quaint queen! A cozy home built in 1900 with a modern esthetic. Located in the heart of Shippensburg, this home is close to Shippensburg University, Luhrs center, and Shippensburg fairgrounds. It is also 30-45 minutes from Carlisle, Gettysburg, Chambersburg, and many state parks including Caledonia and Pine Grove Furnace State Park. The quaint queen is perfect for a business trip, long visit, or short weekend.

Family · Location · Indoor spaces

Quaint Historic Stone House

Conveniently located in downtown Shippensburg and in walking distance to pubs, restaurants and stores, this older rustic home offers modern touches that makes it cozy and comfortable. 45 minutes to popular tourist attractions in Gettysburg, the house is only 5 mins away from Interstate 81. Large fully fenced backyard and personal paved 3 car parking lot behind shed. Only well behaved pets are allowed.

Value · Family · Accuracy

Hot Tub, Fireplace, Ping Pong, State Game Lands

-Quiet wooded property with log cabin -Hot tub and fire pit area -Peaceful surroundings, backed up to state game lands -Living room fireplace, wifi, Roku TV, ping pong table -Two car garage Bed / bath explanation: 6 beds total - 2 queen beds, 2 double beds in the loft overlooking the dining room and 1 sofa bed in the basement of the main cabin. 1 queen bed in the private cottage.

Value · Family · Indoor spaces

Select View Cottage

About the cottage: This home is located on a farm raising black angus cattle. There is a large, well-stocked kitchen where you can cook delicious meals, when you're not visiting the local Amish and Mennonite cafes and bakeries. Take your cooking and dining outside on nice days to our lovely patio dining area and grill! There is also a large backyard with gorgeous sunset views.

Family · Value · Back garden