Vacation rentals in Orrstown

The 1850 Retreat Chambersburg

Welcome to The 1850 House! This beautiful 5 br home located in Chambersburg, PA has as been thoughtfully decorated and designed to ensure that you have everything you need for an entertaining and relaxing getaway full of quality time with your family & friends. The 1850 House is newly renovated with white oak floors and accents throughout, beautiful tile work and a custom kitchen with high-end appliances. 50% off monthly stays! *More information coming soon!* *We ask that all guests sign a ren

Pine Mountain Retreat - Roxbury PA - Peaceful

Nestled in the woods, this family-friendly mountain cabin is a peaceful place to relax and reconnect. Surrounded by trees and fresh air, this cabin is sure to be a fvorite. Enjoy meals together, mornings on the deck, and cozy evenings indoors after a day of outdoor fun. With rustic charm, and a quiet setting, this cabin is perfect for family getaways, weekend escapes, and making lasting memories. Includes a large dining area in the sun porch, several decks, and a large living room w/ firplace.

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

Air Hill Haven

Kick back and relax in this peaceful stylish space. This basement apartment gives you a quiet private space to unwind. It is located in the country between Chambersburg and Shippensburg. Located right beside Letterkenny Army Depot, the Chambersburg hospital and Roxbury camp are nearby. Gettysburg and Carlisle Fairgrounds are each about 30 miles away. There is a private entrance with a covered porch. Relax on a glider while facing the woods and listening to the sounds of nature.

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.

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!

Private 3-bedroom, 2-bath House with Large Yard

Well cared for, recently updated 3-bedroom, 2-bathroom home in private, rural setting with many nearby attractions and amenities including downtown Shippensburg and Shippensburg University; Michaux State Park and Pine Grove Furnace; and Amish and Mennonite culture, food, and shopping. Set up with fully equipped kitchen, two desk/spaces, ample parking (including garage), two smart TV/living areas, laundry facilities, and a screened in patio and plenty of yard space.

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.

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.

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.

A-Frame W/ HOTTub, MountainView,Pickleball/tennis

Welcome to Hilltop Haven A-Frame. Perched on top of the ridge and surrounded by trees, this unique getaway offers breathtaking views, total privacy, and a true connection to nature. Designed for both relaxation and recreation, this home has something for everyone—whether you’re unwinding in the hot tub, gathering around the fireplace, or enjoying a friendly competition outdoors.

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.