Holiday rentals with outdoor seating in Washington County

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.

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.

❤️ Secluded 1940s Romantic Tiny House on the River

Relax and escape to the peace and quiet by the Potomac river, and wake to beautiful romantic views of the river and mountains, in this romantic 200 square foot tiny house situated on 3 acres, 450 feet of river front land. Explore and partake of all the activities on the river and surrounding area, just 1 mile from Shepherdstown. Fish, bike, kayak, tube, or just sit by the river and watch the birds and wild life. Read by the river or in the quiet comfort of the house, w/ some wine on us.

Creekside Retreat at the Jewel Vinsota

Relax in a quiet, curated, pet-friendly art exhibit. Live with paintings & sculptures that are for sale. This garden apartment is tucked into a hillside above a creek, along the Jewel Vinsota Sculpture Trail. Your host/gallery curators live upstairs. The “Artist’s Guesthouse” is next door. The private entrance is down a stone-stepped path. Perfect for 2 w/ the queen bed but room for 3 w/ the living room futon. Fully equipped kitchen. Private charcoal grill and fire pit next to the creek.

Ridge top tiny house - mountain side views

Reconnect with nature in this unforgettable tiny house. Perched on the top of a ridge offers great views of the mountains. Modern contrasting interior with the charm only a tiny house can bring. The mountains from three different states (PA, MD, WV) can be seen from within the tiny house. Sitting on the edge of 275 acres of farmland means you will be sure to hear the turkeys gobble during the daytime or the whippoorwill at night. Relax and enjoy the scenery from the loft bed.

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.

Private Country Club Home

I am an experienced super host with eight years of hosting. I have a charming mother-in-law suite with your own entrance in an upscale country club development. Features a beautiful two acre backyard, a fire pit, outdoor deck and grill, private living room, kitchen, bath, and bedroom. We are just 20 minutes from White Tail Ski Resort and less than an hour to Gettysburg, Antietam Battlefield, the Appalachian trail, and C&O Canal. Come join us for a relaxing stay.

Downtown Modern Studio apartment | History & Dining steps away

Welcome to our modern studio, just steps away from the vibrant heart of Shepherdstown. Whether for a relaxing weekend escape or a university visit, our cozy apartment offers an ideal oasis with a comfortable queen bed, dedicated work area, and walk-in shower. Nestled in downtown Shepherdstown, easily explore downtown, and discover a wide variety of dining options, shopping, and recreational activities, all while being a short walk away from the Potomac River.

The 1763 House - Stay in Downtown Shepherdstown

Welcome to our charming downtown Shepherdstown apartment, originally built in 1763 and nestled in the heart of town. Ideal for getaways, visiting family/friends, or university trips. Enjoy a spacious interior, comfortable living room, state-of-the-art kitchen, and private patio. Our downtown location on the Main Street offers convenient access to a wide selection of restaurants, unique shopping, and the Potomac river, all just a short walk away!

Acorn Acre luxury 3-bed A-frame cabin in the woods

Come enjoy adventures or spend some time in peace and quiet at Acorn Acre. Every detail of this rustic A-frame cabin focuses on your comfort. From the remodeled bathrooms and kitchen to the high-end mattresses, bedding and firepit, you'll have all you need to relax and unwind. If you can't check out completely this cabin has high-speed WIFI and all the amenities you need to work from a beautiful location.

The Log Cabin

A restored 1700's log cabin in a convenient location to Shepherdstown and surrounding attractions. One bedroom upstairs with a queen sized bed. One pull out sofa in the downstairs living area. In the summer of 2018, we have added an intimate brick patio area suitable for alfresco dining and for fireside sitting. It is peaceful. It is beautiful. You will not want to leave.

Last Rodeo Cottage

Our cottage is private where guest can relax; Looking to spend some quiet time out of the city. Close to D.C.and the Historic site of surrounding areas. Close to Charlestown Casinos. Our home is right off I- 81 This cottage is Handicap accessible from private parking to shower and amenities. Lovely park like setting shared with our family pets.