Holiday 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

Beautiful Bell Avenue Retreat

This stylish A-frame home is nestled near farmland. It’s the perfect stay for wedding weekends, bridal showers, graduations, girl getaways, family reunions, Gettysburg tours, regional festivals, and much more. The light in the great room is fantastic for use as a bridal party ready room , and photographers love the house for pre-wedding photos. It’s 10 minutes to Wilson College, 35 minutes to Shippensburg University , 38 minutes to Gettysburg College, and 45 minutes to Dickinson University.

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

Valley View Retreat | Close to Downtown| Sleeps 7

Welcome to Valley View Retreat, a three-bedroom residence located just outside of Shippensburg and only 20 minutes from Chambersburg, this beautiful retreat is the perfect spot for your visit to the area! Recently renovated and improved, this family-friendly property is both stylish and convenient, with a full-size, well-stocked kitchen, two full bathrooms, including one ensuite to a bedroom, a private deck, fast Wi-Fi, a 50" smart TV, hotel-style linens, and parking for up to 3 vehicles!

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.

Peaceful Farm Retreat w/ Views Near Shippensburg

Rolling Hills Symphony is a beautiful home nestled in the peaceful hills of Shippensburg, PA. This home on an Amish farm and is surrounded by the sights and sounds of country life. The living area is all on one level, making it ideal for families with small children or those with mobility issues. There's a kitchen furnished with the necessities for cooking and baking, and there's ample dining space to gather with loved one.

Foot of the Mountain Cottage

History of the cottage: Built in 1998 as a gift shop selling Boyd's Bears, and other home décor, We were ranked one of the top Boyd's sellers in the country. Once we closed the shop, it has been renovated to a rental space. We want it to be a place people can come partake in our beautiful views, see wildlife & enjoy a quiet environment. The Cottage is located adjacent to our home but still give privacy to enjoy the location.

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.

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.