Vacation rentals in Greencastle

The 1780 Cabin on Main

A charming cabin built circa 1780 situated right on Main Street, just steps from Pubs and Restaurants and easy walking distance to historic Mercersburg Academy. There is a separate sleeping area upstairs with a queen-size memory foam bed. The lower level features a foldout couch and air mattress for additional guests, as well as a 55" TV and a wet bar and bathroom. Visitors have universally enjoyed the cabin's cozy feel. While there is no yard available, the town is great for walking dogs.

Private, relaxing, scenic 2 bdrm unit, Sleeps 1-5

My mother said over and over again, “The most beautiful place in Washington County “. Start your day with a brisk walk on a nearly 1 mile path that surrounds the perimeter of this beautiful farmland property. Enjoy your morning coffee as you listen to the birds. Relax in a rocking chair on the gazebo as you watch the sun go down behind the mountains. Less than 10 min from I 70 and I 81 and 20 min from Whitetail Ski. Don't expect everything brand new, but expect everything to be neat and clean.

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-Dogs Only. 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

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. We live upstairs with our two children and two dogs. We maintain quiet hours between 10pm and 7am. Pet friendly, No smoking, No parties.

Turkeyfoot Hideaway!

Turkeyfoot Hideaway is serene retreat and a peaceful escape. This charming cabin has a quiet location with self check in via keypad. We also have walking trails, a lighted fire pit area, gas grill and large deck! We look forward to hosting you! We are just 15 minutes from downtown Chambersburg with lots of unique food and coffee shops! We are just 20 minutes from Hagerstown, MD, just 25 minutes from Whitetail Ski Resort and only 40 minutes from historic Gettysburg! Come find us!

Creekside Cottage

Creekside Cottage is a lovely two-bedroom cottage surrounded by beautiful gardens with a back deck that makes you feel like you are living in a tree house. This is the perfect spot to relax and recharge. There are beautiful views of Back Creek from the deck where you can bird watch and hopefully catch sight of one of our local bald eagles. You'll feel right at home with this spacious kitchen that is well-stocked. Walking distance to Twin Bridge Camp. NO SMOKING NO PARTIES.

Oak Hill Private Suite Historic North End

A recently renovated private suite only 1.5 miles from town center. Welcoming ‘walking’ neighborhood of architecturally diverse homes inspired by the Garden City Movement of early 20th C. Near both Interstate 81 and 70, Museum of Fine Arts, Whitetail Ski Resort, New Baseball Stadium, Antietam, Gettysburg, Frederick, C&O bike trail, wineries, outlets. Guests enjoy stays for tourism, conferences, trainings, the MD Int’l Film Festival, JFK 50, family visits and artist retreats.

The State Line Stay

Our townhome offers the perfect blend of comfort, convenience, and location. Situated on the Maryland/Pennsylvania state line in Greencastle, this home is just minutes from Interstate 81, making it an ideal choice for work travelers, contractors, and guests seeking easy access to surrounding areas. Unlike a hotel, you’ll enjoy the privacy of an entire two-bedroom, 2.5-bath home with a one-car garage and in-unit washer and dryer—perfect for both short and extended stays.

Country Home with a Wonderful View

Welcome to our house in the country. Located on a quiet country road you can sit on the porch and watch the sunset over the Mountains to the west. When the weather is warm, we host goat yoga at our farm with our Nigerian Dwarf Goats. We are located less than nine scenic miles away from Whitetail Resort and Mercersburg Pennsylvania. Cushwa Basin on the C&O Canal is less than 14 miles away. We are also a short drive away from Antietam and Gettysburg National Battlefield.

The Study on Main Located on the Square!

Stylish apartment at this centrally-located Study on Main St! With painted exposed bricked, original hardwood floors, a full kitchen with quartz countertops, heating and AC. You will love this stylish yet comfortable space located in the heart of downtown Chambersburg, close to coffee shops, restaurants and shopping, the courthouse and our public library! *We ask that all guests sign a renters agreement and hold a $100 security deposit upon booking in case of damages*

Boxed Inn ~ Hot Tub ~ Fire Pit

This charming, tiny home offers the perfect blend of cozy comfort and the great outdoors, all while nestled close to the Whitetail Resort. Inside is an open space bathed in natural light, where modern style meets mountain tranquility. The interior, with its thoughtfully designed features, comes with a comfortable loveseat, a smart TV, and bar seating: perfect for those intimate conversations or just catching up after a busy day on the trails.

Blissful Camping

Tankless water heater. Never run out of hot water. You’ll treasure your time at this memorable place. A quiet place to get away and explore the area. This is great for traveling professionals as a home away from home. Enjoy a comfortable outside area along with the inside that has all the amenities of a home. A firepit to have nightly fires on those days when it's not so hot or not too cold.