Holiday rentals in Greencastle

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Top-rated holiday rentals in Greencastle

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Top guest favourite
Home in Greencastle
4.97 out of 5 average rating, 378 reviews

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

Top guest favourite
A covered patio area is presented with a picnic table and a decorative rug. Lush flower beds filled with vibrant blooms line the space, adding color and charm. A small wooden chair enhances the inviting outdoor setting.
Flat in Hagerstown
4.99 out of 5 average rating, 145 reviews

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.

Top guest favourite
Flat in Falling Waters
4.95 out of 5 average rating, 215 reviews

Near I-81, but private! Laundry! No fees!

Welcome to your peaceful retreat! This spacious and clean apartment features a fully equipped kitchen, dual shower heads, a cozy living area, and a washer/dryer for your convenience. Ideal for travelers seeking a quiet getaway or a stopover along I-81, our home is close to Antietam Battlefield, Hagerstown Shopping Outlets, C&O Canal, Tomahawk MotoX, Greenbrier State Park, Shepherdstown, and Harper's Ferry. Enjoy a comfortable stay with thoughtful amenities designed to make you feel at home!

Top guest favourite
The treehouse is perched among tall trees, featuring a wooden deck that wraps around its structure. A gentle staircase leads to the entrance. In the foreground, purple flowers bloom beside a rock outcropping, enhancing the natural landscape under a bright blue sky.
Treehouse in Shepherdstown
4.97 out of 5 average rating, 390 reviews

Cozy West Virginia Treehouse

Thanks for checking out our treehouse! It’s 4 minutes from downtown Shepherdstown and 15 minutes from downtown Harpers Ferry. We are excited to share it with other fun-loving folks! The treehouse has heat and AC, a tiny kitchen with a mini fridge, stove top, toaster oven, gravity-fed sink and kitchenware. There’s a bathhouse built on the back of the host’s home with a conventional toilet and shower. There’s also an outhouse with a light and essentials. We provide wood for the fire pit also.

Top guest favourite
Place to stay in Shippensburg
5 out of 5 average rating, 449 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

Superhost
A dining area with a wooden table is surrounded by eight matching chairs, featuring a centerpiece of fresh flowers. Soft lighting is provided by a pendant lamp. A staircase with a black railing is visible, leading to a cozy living area with a dark sofa and art on the walls.
Home in Waynesboro
4.82 out of 5 average rating, 239 reviews

Waynesboro Adventure with the Family

The cozy house for the whole family, dogs included. Quietly located in the town of Waynesboro, a short walk to downtown and excellent Sushi - Sapporo. Eat in or explore Waynesboro's charm. 1.5 hours from Baltimore or Washington DC. 23 miles from Historic Gettysburg. 13 miles from Ski Liberty and 23 miles from Whitetail Ski resorts. Covered carport parking. Perfect for the family vacation or ski trip. Stocked with toys and games. Full line of baby amenities available upon request.

Top guest favourite
The entrance to The Crooked Cottage is framed by wooden planks and surrounded by greenery. Two windows offer glimpses into the inviting interior, while a gravel pathway leads up to the door, playfully adorned with a sign featuring the name of the cottage.
Home in Myersville
4.98 out of 5 average rating, 282 reviews

The Crooked Cottage: a Cozy, Curated Escape

You will instantly relax in this stylish, pet-friendly home only 8 mins from I-70, exit 42. Under a canopy of trees find a beautifully landscaped yard with decks and two fire pit areas. Enjoy the well-apportioned kitchen with organic, fair trade coffee. Relax with 2 Roku TVs, games and puzzles, bathe with soaking salts and Turkish towels. For outdoor enthusiasts, pitch your tents. Sit by the wood-stove in the winter, or lay in a hammock when it’s warm. Welcome to The Crooked Cottage!

Top guest favourite
The A-frame cottage features a striking wooden exterior with a stone chimney. Large windows provide views of the surrounding greenery, while manicured shrubs and ornamental grass add to the landscaping. The structure's design is complemented by a clear blue sky overhead.
Cabin in Chambersburg
4.95 out of 5 average rating, 251 reviews

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!

Top guest favourite
The entrance features a welcoming porch area surrounded by colorful potted plants and flowers. A wooden rocking chair sits on the deck, complemented by a textured area rug. Double doors with grid-patterned glass provide access to the suite, framed by lush greenery.
Guest suite in Hagerstown
5 out of 5 average rating, 510 reviews

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.

Guest favourite
A white farmhouse is set against a backdrop of open green fields under a partly cloudy sky. A porch with a few chairs is visible at the front, and a small grill is placed on the lawn nearby. A clear pathway leads to the house.
Farm stay in Chambersburg
4.94 out of 5 average rating, 133 reviews

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!

Guest favourite
A polycarbonate dome is nestled among trees, illuminated in soft green light. The spacious deck includes a seating area and a small table. A colorful sunset is visible in the background, casting a warm glow over the Appalachian landscape.
Dome in Shippensburg
4.91 out of 5 average rating, 147 reviews

Spectacular views, intimate dome

Come experience a truly one of a kind polycarbonate dome tucked away in the Appalachian mountains! Situated on the mountainside overlooking the scenic Cumberland valley. Complete privacy, stunning sunsets, and amazing amenities! The dome is climate controlled. The spacious deck is equipped with a meticulously maintained hot tub, and a blackstone griddle. This offers the unique opportunity to be immersed in nature, yet enjoy numerous amenities and comfort.

Guest favourite
An A-frame cabin surrounded by lush greenery features two expansive decks. The front deck includes seating and a decorative railing, inviting relaxation while enjoying the natural setting. Floor-to-ceiling windows allow for ample natural light, enhancing the connection with the surroundings.
Cabin in Hedgesville
4.9 out of 5 average rating, 202 reviews

Unique Gem: Cozy A frame cabin in the woods

Come unwind and enjoy nature in this cozy, quaint, A-frame cabin. Nestled in the woods overlooking a community pond, enjoy the views through floor to ceiling windows or relax outside on one of the two large decks. The home includes a gas grill available for use and fire pit with wood provided. Best suited for two guests, it can accommodate up to 4 with use of the futon in the loft. Located just minutes away from the Potomac River and numerous recreational areas!

Popular amenities for Greencastle holiday rentals