Holiday rentals in Shady Grove

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Top-rated holiday rentals in Shady Grove

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Top guest favourite
Guest suite in Mercersburg
4.94 out of 5 average rating, 561 reviews

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.

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, 169 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
Home in Greencastle
4.97 out of 5 average rating, 420 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-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

Guest favourite
Two classic wooden Adirondack chairs are positioned near the bank of a gently flowing stream. Lush greenery surrounds the area, with trees casting dappled sunlight on the water. A clear blue sky adds a serene backdrop, enhancing the peaceful atmosphere of the outdoor space.
Cottage in Waynesboro
4.94 out of 5 average rating, 139 reviews

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.

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, 429 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
A tree-lined driveway leads to a charming home, partially obscured by lush greenery. Sunlight filters through the leaves, casting gentle shadows on the well-maintained lawn. The sky is bright with fluffy clouds, contributing to a serene, inviting atmosphere.
Home in Hagerstown
4.78 out of 5 average rating, 169 reviews

Private Country Club Home

We are experienced super hosts with over 9 years of hosting. We have a charming mother-in-law suite with your own entrance in an upscale country club development. Features a beautiful large backyard, a fire pit, an outdoor deck and grill, a private living room, a kitchenette, a private bath, and a bedroom. We are just 30 minutes from White Tail Ski Resort and less than an hour to Gettysburg, Antietam Battlefield, the Appalachian Trail, and the C&O Canal. Come join us for a relaxing stay.

Top guest favourite
An expansive open-concept living area is highlighted by large windows, providing ample natural light and panoramic views of the surroundings. Comfortable seating areas are arranged around a central coffee table, while a cozy stone fireplace serves as a focal point against a feature wall.
Home in Smithsburg
4.96 out of 5 average rating, 222 reviews

The Great Escape Lodge ~ Exquisite Mountain Views

The Great Escape Lodge is a soaring A-frame offering luxury accommodations. Owner designed and custom built in 2022, this luxury getaway is nestled in the stunning Catoctin Mountains with views parallel to those seen on Paramount's hit series Yellowstone. This exquisite residence offers outstanding interior and exterior custom touches and amenities. From the open concept great room to the massive deck with rockers and hot tub, there are endless opportunities to enjoy the scenic views.

Top guest favourite
The exterior of a one-story cottage is shown, featuring a combination of green siding and a dark metal roof. A neatly landscaped front yard includes shrubs and seasonal foliage. A paved walkway leads to the front door, flanked by two windows, and a double garage is visible on the left.
Cottage in Chambersburg
4.93 out of 5 average rating, 104 reviews

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.

Top guest favourite
The exterior of the house is shown, enhanced by a blanket of snow. A welcoming porch features two rocking chairs, while snow-covered shrubs line the path to the door. A soft glow from the sunset is visible in the sky beyond the property.
Farm stay in Greencastle
4.94 out of 5 average rating, 148 reviews

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.

Top guest favourite
A stylish living area features a cozy sofa facing a modern coffee table. Black walls provide a dramatic backdrop to the space, complemented by golden curtains framing large windows. A sleek bookshelf and a decorative fireplace enhance the room's character, while a circular rug adds warmth.
Flat in Chambersburg
4.93 out of 5 average rating, 160 reviews

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*

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
4.92 out of 5 average rating, 166 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.

Top guest favourite
A charming tiny home is nestled among tall trees, featuring a modern exterior with a combination of white siding and natural wood accents. A small deck is visible, adorned with potted plants, inviting relaxation in a serene natural setting.
Tiny home in Mercersburg
4.98 out of 5 average rating, 199 reviews

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.

Popular amenities for Shady Grove holiday rentals