Holiday 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.

Antietam Toll House~an historic waterfront cabin

The Antietam Toll House (@antietamtollhouse) is a renovated historic property circa 1800. Sitting on the bank-head of the Antietam stream, this cabin has it's own private fishing hole. Secluded, yet close to amenities and attractions, this property is the perfect place for an artist retreat, respite from the city or a base from which to explore local gems of the area. Wineries, Appalachian Trail, Antietam, Gettysburg battlefields, Ski Liberty, Catoctin , Cunningham Falls and more nearby.

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.

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.

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 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 I81, it’s a favorable location but private setting. Within 10-20 minutes of Chambersburg restaurants, shopping, hospital and activities. Also about a 30 minute drive to historic Gettysburg, PA! The farm is active with 2 cows and 3 (way too friendly) cats. We are a small family wanting to share out beautiful piece of land with all who visit!

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.

Colonial Era Spring House

A unique and private mountain top colonial era spring house, with two springs flowing thru the basement. Originally the site of a tannery in the 1700s. Here you can relax, recharge, and rejuvenate. We celebrate all four seasons where you can enjoy Mother Nature's ever changing scenery at 1300' above sea level with fresh mountain air. Our area offers many things to do, or you may choose to stay in and do nothing at all.

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.