Holiday rentals in Shippensburg

4.99 out of 5 average rating, 103 reviews

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."

4.92 out of 5 average rating, 132 reviews

Flat in Chambersburg

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

4.94 out of 5 average rating, 125 reviews

Home in Chambersburg

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.

Place to stay in Shippensburg

5 out of 5 average rating, 375 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

4.95 out of 5 average rating, 234 reviews

Cabin in Chambersburg

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!

4.99 out of 5 average rating, 169 reviews

Flat in Chambersburg

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.

4.96 out of 5 average rating, 223 reviews

Cottage in Spring Run

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.

4.97 out of 5 average rating, 971 reviews

Guest suite in Carlisle

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.

4.9 out of 5 average rating, 188 reviews

Home in Chambersburg

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.

4.94 out of 5 average rating, 337 reviews

Flat in Carlisle

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.

Apartment in Chambersburg

4.97 out of 5 average rating, 394 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.

4.99 out of 5 average rating, 138 reviews

Cottage in Biglerville

Copper Flat Cottage

Welcome to Copper Flat Cottage! Enjoy your time on top of the mountain in our lux studio cottage. We are within walking distance of the Appalachian Trail, and within half a mile of the DCNR ATV trails. We are located 15 min. from I81 and Shippensburg. Experience life on the mountain in this romantic getaway. We are glad you are here!

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Other great holiday rentals in Shippensburg

5 out of 5 average rating, 8 reviews

Select View Cottage

JackieRating, 5 stars3 weeks ago

This was the nicest Airbnb we’ve rented in a long time! I’ve already booked our next stay. The location is perfect for us, near family, and the view is indeed lovely. It was super clean, the pictures let you know exactly what to expect. The beds were very comfortable and there were little notes with tips for any questions that arose while we were there! We especially loved all of the real house plants! It made it feel so cozy. They’re serious about the Mennonite buggies arriving to church on Sunday morning! It was the most horse and buggy traffic I’ve ever seen!

Flat in Chambersburg

5 out of 5 average rating, 3 reviews

Air Hill Haven

KateRating, 5 stars1 week ago

This was exactly what we needed. Very cute space with everything you would need! My boyfriend and I were traveling long distance and wanted a quiet place to rest before we continued the rest of our trip and this place was exactly that (thank you for same-day booking options). I would highly recommend this place as feels like home. Very well done and I wish you success for your future bookings!

5 out of 5 average rating, 21 reviews

Spacious Shippensburg Home, Close to Museums!

MarkRating, 5 stars2 weeks ago

Beautiful spot, friendly neighborhood.Great place to stay.

4.88 out of 5 average rating, 76 reviews

Barn in Chambersburg

A Studio Barn Apartment at DuCar Farm

GlennRating, 5 stars1 week ago

The place is what we expected. The stone walls and floor are unique. Although there is a train track nearby, the walls really deadened the sound, so we slept well. A peaceful stay in the country, but plenty of restaurants within 20 minutes. The internet was good enough for e-mail, but I would not try to work from here (that is a good thing when trying to unplug for a few days). The space is a bit dark (but I am partial to brightly lit locations), but it is a stone walled barn, so about what you might expect. We were there to visit family in the area, so it was a place to relax and sleep, and it met that need well.

5 out of 5 average rating, 11 reviews

1789 Historic Gem | Modern for 9

JeremyRating, 5 stars3 weeks ago

Our stay at this incredible 1700s house was absolutely perfect! From the moment we arrived, we were charmed by its historic character and cozy atmosphere. The house is beautifully maintained, blending its original features with all the modern comforts we needed. We loved exploring all the unique nooks and crannies, imagining the centuries of stories within its walls. The location was ideal for our plans, and we found ourselves completely relaxed and at home. It truly felt like stepping back in time in the best possible way. We highly recommend this unique Airbnb to anyone looking for a memorable and enchanting getaway!

4.98 out of 5 average rating, 48 reviews

Cottage in Shippensburg

Secluded 14 Acre Entire French Farmhouse & Stream

BrittanyRating, 5 stars3 weeks ago

Tamela’s place was so great! The house was beautifully decorated and the kitchen had everything we needed. The landscaping was also beautiful. We loved walking down to the stream and exploring. The beds were really comfortable too!

Private room in Chambersburg

4.95 out of 5 average rating, 103 reviews

Robin’s Creekside Retreat

MikeRating, 5 stars3 weeks ago

Sweet ideal getaway if you want to just get away and relax. Comfy and cozy, we felt like we didn't want to leave. Robin was very helpful with any questions we had. It's in the middle of the countryside but has plenty of shopping and restaurants not too far away. My wife and I loved it. Mike