
Holiday rentals in Shippensburg
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Top-rated holiday rentals in Shippensburg
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Old Homestead...Rest, Relax and Renew at this Quant Getaway
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."

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

Legacy Bridge Farmhouse
This cozy farmhouse was built in the 1800's and has been completely remodeled. The house is completely furnished and the large kitchen is fully stocked for cooking. The house sits on a beautiful farm property. There is a stream that runs through the property and there is a beautiful view from the back porch. It is located 10 minutes from Shippensburg and Chambersburg. It is also about 30 minutes from Gettysburg Battlefield. Whitetail, Ski Liberty Resort, and Roundtop are all within an hour.

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

Cedarhill Cottage
Nestled in Franklin County, this quaint A-frame cottage is a perfect destination. If you are looking for a place to get away and defrag from your busy life, this newly remodeled A-frame cottage offers all the comforts of home in a quiet area that has been described as refreshing and renewing. Surrounded by views and the sounds of nature and within minutes of local shopping and dining - you’ll quickly see why our guests become family. Sit by the fire pit and make some s'mores!

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.

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.

Pup Friendly Private Space
Welcome, I am Debbie a busy Mama/Grandma with a bunch of millennial children (plus five grandchildren and 5 granddogs). I am excited to be able to offer my beautifully designed space close to Dickinson, the War College, Carlisle Fairgrounds, Appalachian Trail, Harrisburg and Gettysburg. You have your own off-street parking, private entrance and a large bedroom/sitting room with full private bathroom and a microwave/ mini-refrigerator for your convenience.

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.

Quiet, Cozy, Contemporary
Tucked away behind the main road, this “Fairgrounds Flat” studio apartment is centrally located in historic Carlisle Borough. Sparkling clean, contemporary stying, and filled with amenities, you will feel you are at a home-away-from-home. Enjoy a quiet evening on the beautifully arbored deck. An easy ten minute walk will bring you to the heart of downtown where everything is at your fingertips.

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.

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.
Popular amenities for Shippensburg holiday rentals
Other great holiday rentals in Shippensburg

Turkeyfoot Hideaway!

Quaint Historic Stone House

Welcome to Creekside Anglers

Private Suite with Stunning Views

Serenity Spaces Guest House

Purple Kangaroo Cottages

Townhouse on King

Prince Street Suite
Quick stats about holiday rentals in Shippensburg

Nightly prices starting at
Shippensburg holiday rentals start at $78 SGD per night before taxes and fees

Verified guest reviews
Over 110 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Shippensburg rentals

5 Average rating
Shippensburg stays are highly rated by guests – averaging 5 out of 5!
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- Hersheypark
- Cunningham Falls State Park
- Liberty Mountain Resort
- Whitetail Resort
- Codorus State Park
- Cowans Gap State Park
- Caledonia State Park
- Hershey's Chocolate World
- The Links at Gettysburg
- Gambrill State Park
- Berkeley Springs State Park
- Gifford Pinchot State Park
- Roundtop Mountain Resort
- South Mountain State Park
- Pine Grove Furnace State Park
- Brookmere Winery & Vineyard Inn
- SpringGate Vineyard
- Whiskey Creek Golf Club
- Adventure Sports In Hershey
- Big Cork Vineyards
- Catoctin Breeze Vineyard
- Black Ankle Vineyards
- Adams County Winery
- Linganore Winecellars




