Vacation rentals in Orrstown

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Top-rated vacation rentals in Orrstown

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Guest favorite

Home in Newburg

4.97 out of 5 average rating, 113 reviews

Cozy Country apt.

Tucked away beside the Country store cafe, in beautiful Cumberland valley, this charming and cozy country style appt is perfect for a getaway or a nights rest from work or travel. Its located a few miles off of the PA turnpike and 7 miles from Shippensburg. The outside has a private backyard lined with pine trees and a patio perfect for morning coffees and bird watching. The cafe next door serves delicious Breakfast lunch Fresh baked goods and Homemade bread daily. Cafe Hrs are Mon-Sat 6 to 2:30

Guest favorite

Rental unit in Chambersburg

4.91 out of 5 average rating, 113 reviews

The Study on Main Located on the Square!

Enjoy this stylish apartment at this centrally-located Study on Main St! With hints of painted exposed bricked, original hardwood floors, a full kitchen with new quartz countertops, heating and AC, we know you will love this stylish yet comfortable space we have put together for you! You will be in the heart of downtown Chambersburg, steps away from coffee shops, local favorites for food and shopping, art galleries, the courthouse and our public library! *We ask that all guests sign a renters a

Guest favorite

Home in Chambersburg

4.85 out of 5 average rating, 227 reviews

LastMinuteBookings+OutdoorDining+5minToDowntown

This stylish & modern family-friendly home offers ample space & comfort for the whole group. Conveniently located just 5 minutes from downtown Chambersburg & about 25 miles from the Gettysburg Battlefields. Minutes from I-81 ★Perfect for families & traveling professionals★ The living area is on one level & great for quality time together, whether you're enjoying a home-cooked meal in the fully-equipped kitchen or cozying up in the invitingly furnished lounge area We look forward to hosting you!

Guest favorite

Place to stay in Shippensburg

5 out of 5 average rating, 322 reviews

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

Guest favorite

Rental unit in Chambersburg

5 out of 5 average rating, 131 reviews

REmix REtreat, curated and styled by REmix Design

Enjoy downtown Chambersburg in this biophilic, sustainable loft, central to local shops, restaurants, breweries, and coffee shops. The building that houses the loft was erected in the 1890s, giving the space charm unique to the era. Wander down Main St get a feel for our quaint downtown. There is a rail to trail within one block of the space for exercising and biking. Chambersburg is a thirty minute drive to Gettysburg, and less than two hours from Baltimore and Washington DC.

Guest favorite

Farm stay in Chambersburg

4.94 out of 5 average rating, 104 reviews

The Little White House

Relax on the farm with a peaceful view and rural atmosphere, with the convenience of being close to local attractions. Located close to I81, it’s a favorable location but private setting. Within 10-20 minutes of Chambersburg restaurants, shopping, hospital and activities. Also about a 30 minute drive to historic Gettysburg, PA! The farm is active with 2 cows and 3 (way too friendly) cats. We are a small family wanting to share out beautiful piece of land with all who visit!

Guest favorite

Cottage in Spring Run

4.95 out of 5 average rating, 197 reviews

Cozy country charm

My cottage has beautiful views from every side of the house and a relaxing front porch to sit and relax and enjoy a cup of coffee. It's a cozy cottage at the foot of the mountain with lots of privacy. There are no neighbors. There are horses here to enjoy watching them graze or feed them a snack. It's truly a nice getaway and still only a half hour from 3 local towns. For warmer weather there is a firepit, picnic table, grill and some nice shaded areas to relax.

Guest favorite

Home in Chambersburg

4.91 out of 5 average rating, 166 reviews

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.

Guest favorite

Train in Shade Gap

4.93 out of 5 average rating, 149 reviews

Authentic Caboose 10 min to historic EBT Railroad

Enjoy the natural beauty surrounding this historic getaway. This getaway includes many amenities for you to enjoy. ~10 minutes from train and trolley rides~ ~On 5 acres along a country road~ ~Heat and AC~ ~Hot Showers in the Caboose~ ~BBQ Grill~ ~Queen Bed and two singles in the loft~ ~Coffeemaker~ ~Microwave~ ~Refrigerator~ ~WIFI is coming soon~ ~Fire ring with firewood~ ~Picnic Table~ ~Toaster~ ~WIFI~ ~Smart TV~

Guest favorite

Condo in Chambersburg

4.98 out of 5 average rating, 295 reviews

One-bedroom apartment with separate entrance.

Adorable one-bedroom apartment with separate entrance. Located 10 minutes from downtown Chambersburg. Whether its historical sight-seeing, culturally diverse restaurants, or local craft beer, there is plenty to see and do in this area. Built in 2021, this apartment is on the lower level of our custom built home. It also has a fully equipped gym. Pet friendly, No smoking, No parties.

Guest favorite

Guest suite in Chambersburg

4.88 out of 5 average rating, 172 reviews

Cute Place Just Out Of Town With A Country Feel

Looking for an affordable place to stay the night or a few days? You may have just found the perfect place. This cute efficiency unit may just cover all the bases you need for a short stay. What once was a office for a shop, is no longer needed as an office and so it was converted to supply a place to sleep for tired travelers or for people looking to get away for a few days.

Guest favorite

Guesthouse in Gettysburg

4.99 out of 5 average rating, 416 reviews

The Cock and Feather Guesthouse

PLEASE READ ALL OF THE HOUSE RULES BEFORE BOOKING YOUR RESERVATION. OUR CALENDAR IS CURRENTLY OPEN THROUGH DECEMBER 14. WE WILL BE CLOSED FOR THE WINTER SEASON FROM DECEMBER 15 THROUGH MARCH 31, 2025. PLEASE CHECK BACK IN EARLY MARCH FOR AVAILABILITY BEGINNING ON APRIL 1.