Vacation rentals in Greencastle

Country 2-Bed/2-Bath Barndominium-Dogs Welcome

Pets Welcome - Dogs Only. 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. 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

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.

The Quick Escape

Welcome to your Quick Escape! *prof. photos & more updates soon* This cozy duplex offers a fenced in yard, lovely rooms & open living space for you to enjoy food, games and gathering together! The spacious bedrooms offer airy, bright feels so you can relax and feel at home during your stay Indulge in the outdoor space by catching the sunrise on the patio or stay warm by the fire! The home is in a prime location for food, shopping, skiing, golfing, and if you just need a quick place to stay!

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.

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 treadmill in the 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.

Beautiful 5 star Mansion, Pool, Home Theater

Nestled on 3 beautifully landscaped acres, this 7-bedroom, 5.5-bath mansion offers the utmost privacy and modern comfort, sleeping up to 32 guests. With over 5,000sf of space, +2500sf enjoy one or two full kitchens (depending on group size, additional charge applies) home theater with Bose surround sound, and a lush backyard with a swimming pool, gazebo, and scenic pond. Additional amenities include an indoor pool table, outdoor dining area with a propane gas grill, and dedicated workspace.

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 I-81, it’s a favorable location but private setting. Within 20 minutes of Chambersburg restaurants, shopping, hospital and activities. Also about a 40 minute drive to historic Gettysburg, PA! The farm is active farm growing row crops and hay. We have a very friendly barn cat! We are a family wanting to share our beautiful piece of land with all who visit!

Unique historic home - Springhouse 1803

If you are looking for a unique place to stay, come visit us at Springhouse 1803. Yes, there really is a spring under the house. After sitting empty for 20+ years, the house has been restored to be lived in again and it has maintained much of its colonial charm. The house has all the amenities you need for a comfortable stay. NOT A PARTY HOUSE, OWNER IS ON SITE in separate house. If you're looking for a day that is blocked, you can inquiry if it's available, see below for more details.

Cedarhill Cottage with Cozy Fireplace

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!

Rosemont Mansion | Group Stays & Events

Welcome to Rosemont Mansion, a beautifully restored 1909 estate in historic Mercersburg. Designed for group stays, celebrations, and meaningful time together, it blends historic charm with modern comfort. Walk to cafés and enjoy spacious gathering areas. Ideally located: 2 min to Mercersburg Academy, 10 min to Whitetail Resort, 1–2 blocks to restaurants and coffee shops, and 15 min to Buchanan’s Birthplace State Park, with easy access to wineries, hiking, and scenic drives.

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.