Holiday rentals in Shady Grove

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Top-rated holiday rentals in Shady Grove

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Home in Greencastle
4.97 out of 5 average rating, 426 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

Top guest favourite
A cozy living area is featured, showcasing a wooden entertainment unit with a television. A green armchair and a dark gray sofa are positioned for comfort. Natural light filters through the window, highlighting the light wood flooring and decorative accents.
Apartment in Chambersburg
4.97 out of 5 average rating, 598 reviews

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.

Top guest favourite
The exterior of the historic colonial house is depicted, showcasing a light stone facade complemented by a slanted metal roof. A spacious front porch with a wooden railing is visible, surrounded by a well-maintained garden featuring various plants. Two doors lead into the home.
Cottage in Hagerstown
4.96 out of 5 average rating, 465 reviews

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.

Top guest favourite
Cabin in Chambersburg
4.98 out of 5 average rating, 58 reviews

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!

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, 256 reviews

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!

Top guest favourite
Townhouse in Greencastle
5 out of 5 average rating, 22 reviews

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.

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, 162 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, 173 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
Cabin in Waynesboro
4.94 out of 5 average rating, 16 reviews

Nature lovers dream, A-Frame on a farm-king bed

Wake up to wild life sightings or unwind after a day of work or adventure in this secluded cabin conveniently located near several hospitals and major businesses/corporate hubs. Just a short drive to two Ski resorts, the Appalachian trail, Michaux state forest, Hershey, Gettysburg, and Antietam battlefields. Perfect for romantic getaways, weekend escapes, outdoor enthusiasts, traveling healthcare providers, and Buisness travelers needing a peaceful stay.

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, 201 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.

Top guest favourite
The exterior of a colonial era spring house showcases a natural stone base supporting a wooden structure. A spacious balcony with wooden railings extends from the second floor. Brightly colored hanging flower pots add a touch of greenery to the inviting façade.
Home in Blue Ridge Summit
4.99 out of 5 average rating, 668 reviews

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.

Top guest favourite
The interior of a spacious RV is displayed, featuring a cozy seating area with a light-colored couch and a kitchen equipped with modern appliances. A rustic dining table is set with plates and glasses, while natural light filters in through window coverings. Wood cabinetry and elegant accents are visible.
Camper van/Motorhome in Chambersburg
4.93 out of 5 average rating, 44 reviews

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.

Popular amenities for Shady Grove holiday rentals