Holiday rentals in Orrstown

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

4.97 out of 5 average rating, 306 reviews

Home in Greencastle

Country 2-Bed/2-Bath Barndominium w/Beautiful View

Rural agricultural setting but convenient to towns, golfing, Whitetail Ski Resort and civil war historical sites. Two bedrooms with queen beds w/linens, two full baths, full kitchen living room area, desk and outdoor firepit and chairs (firewood for additional fee). Queen pull-out sofa bed. Wi-Fi and HDTV. Paved drive/parking area. Pets welcome w/agreement. Short drive to I-81 and I-70 20 mins to Hagerstown 15 mins to Chambersburg 20 mins to Whitetail Ski Resort 1.5 hrs to Baltimore/Washington

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, 373 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

Cabin in Berkeley Springs

4.98 out of 5 average rating, 118 reviews

Monte Vista~Golf~Views~PS5~Sport Court~EV Charger

IG @montevistawv Luxury Getaway Professionally Designed for STR 🏔️Massive Panoramic 3 State View 🏌️‍♂️Golf Ball Driving Range 🏀 Pickleball, Basketball, Volleyball & Tennis 🎮 PlayStation 5 Mini Disc ♨️ 6-Person Hot Tub 🔊Sonos Sound Throughout 🔋Level 2 EV Charger 🥾 Hiking Trail on site 🌳 33 private acres, no quiet hours 🔥 Massive Firepit + Grill & Pizza Oven 🛋️ Cozy Gas Fireplace 🌐 Fast WiFi & Three 65" Smart Tvs 🛏️ 3 King Beds & Twin Bunk Bed 💼 Dedicated Work Area

4.99 out of 5 average rating, 166 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, 220 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.

4.9 out of 5 average rating, 187 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.

4.85 out of 5 average rating, 252 reviews

Home in Chambersburg

LastMinuteBookings+OutdoorDining+5minToDowntown

This stylish and modern family-friendly home offers a welcoming and spacious retreat for your entire group. Conveniently located just 5 minutes from downtown Chambersburg and about 25 miles from the historic Gettysburg Battlefields, The Cheerful Abode provides the perfect base for exploring the area’s rich history and scenic attractions. Plus, it's just minutes from I-81, making it easy to get around and enjoy all that the region has to offer.

Apartment in Chambersburg

4.97 out of 5 average rating, 391 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 suite in Chambersburg

4.89 out of 5 average rating, 192 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.

4.99 out of 5 average rating, 137 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 Orrstown

5 out of 5 average rating, 8 reviews

Home in Blain

The Enslow Bridge House- creek front country home

RachaelRating, 5 stars2 weeks ago

House was very remote, but there was a small store about 10 min away for essentials. We planned our meals, shopping and excursions in advance, so we really didn't need to make any special trips. House was huge and had everything we could of needed. The Co-Host reached out to us a couple of times about mowing and opening the pool, making sure we were OK with it. We had a beautiful rainbow 🌈 to admire and the serenity of the home was exactly what we needed to reset. On the last night our Co-Host brought us a homemade Strawberry pie. I highly recommend this rental for anybody looking to sit back, relax and enjoy the quietness of the area.

5 out of 5 average rating, 6 reviews

Select View Cottage

WendyRating, 5 stars3 weeks ago

We spent one night at JoEllen's place during our trip from New Jersey to North Carolina, and wish we could stay longer! The cottage is only several minutes drive to downtown Shippensburg and surrounded by green farmland. We enjoyed our delicious breakfast (from an Amish eatery at the Maplewood Farm market) on the deck in the backyard, and the beautiful views!

4.95 out of 5 average rating, 42 reviews

Home in Newville

Songbird Hollow

LoriRating, 5 stars6 days ago

We were in the area for a FORD car show in Carlisle and the location was great. Very peaceful. Be sure to check out the King's Bakery there nearby.

Superhost

ChristineRating, 5 stars1 month ago

Rolling Hills Symphony

I don't know how to describe our stay- exceptional! It was very cozy, peaceful, and had stunning views around the home. Not only that, the bedding and linens were high quality. If one is looking for a place of rest, look no further. The tranquility is hard to beat. In meeting the home owners we found them kind, attentive, and delightful. On check in, the place was clean and amply stocked with coffee.

4.96 out of 5 average rating, 25 reviews

Flat in Chambersburg

Main St Modern Suite | Washer&Dryer + Fast Wi-Fi

SusanRating, 5 stars4 months ago

The loft was comfortable and inviting and just as described in the listing. It was clean…immaculate to be more precise😊 and Brett and Jen were quick to respond and communication was a breeze. The location is perfect with restaurants and shopping just steps outside the front door. We look forward to staying at the loft again on our next trip to Chambersburg.

5 out of 5 average rating, 20 reviews

Spacious Shippensburg Home, Close to Museums!

ChristineRating, 5 stars1 month ago

What a comfortable place for 5 adults and 1 toddler! We loved our stay here. You can tell that the renovation of the home was a work of love. It's beautifully done and has everything you would need. They even offered a pack and play for our toddler! There were also plenty of games which we loved. Great for family time. We also loved that there was a community swing across the road; our toddler had so much fun with it. Would definitely recommend!

5 out of 5 average rating, 10 reviews

1789 Historic Gem | Modern for 9

JeremyRating, 5 stars2 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!