Holiday rentals in Washington County

Historic Scrabble, Shepherdstown

The perfect private guest cottage situated beside a beautiful historic home in the unique community of Scrabble Unincorporated just a half-mile from the Potomac River. Modern, comfortable and tastefully decorated with full amenities and parklike surroundings with an abundance of nature at your doorstep. Close to Shepherdstown / Shepherd Univeristy (12 minutes), Martinsburg (20 minutes), Harpers Ferry (20 minutes) and in the heart of civil war history including the famed Antietam National Park.

Romantic, hot tub, king bed, private, pet-friendly

Uniquely spacious escape for couple, small family, or solo traveler. 30-foot great room, wall of windows facing large deck, oak floors NEW HOT TUB in private setting. King bedroom with en suite bath; loft has twin bed. Modern with touches of mcm & vintage create a magical retreat for you in the treetops. On 2 acres. Hike to top of Cacapon Mountain from back door. Quick drive (3 mins) to private community pool/hot tub/tot pool (summer only). 10 minutes to Berkeley Springs with Roman Baths, arts s

Studio: Downtown Hideaway & Waterside Garden Oasis

Our modern studio is on the Town Run and steps away from downtown Shepherdstown. Whether you’re here for a relaxing escape or a university visit, listen to a waterfall from our cozy, zen, spa-like space with outdoor gardens. It’s an oasis with a comfortable full bed, dedicated work area, and walk-in shower. Nestled in historic downtown, you can easily explore German St., with a variety of dining options, shopping, and outdoor activities a short walk away from the Potomac River and C&O tow path.

❤️ 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.

Spruce Run Cottage, Farm stay on Catoctin Mountain

The cottage is located on 25 acres of mostly wooded terrain off Highway 17 near Wolfsville, Maryland, less than an hour and a half from D.C. The cottage faces the woods and the private drive down to the creek. There is almost zero light pollution at night so stargazing is incredible from the balcony. The hosts live on the property up the hill in an 1890’s chink log cabin. Although you can see our house, the cottage feels very private and is a quiet comfortable retreat in the hills.

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 Cozy Villa

Home away from home, conveniently located seconds away from Interstate 81 and central to all restaurants and shops! Perfect for a group of traveling friends or a family looking for a peaceful stay. This warm and cozy villa boasts tastefully modern features with 2bdr, 1bth, fully equipped kitchen, living room, dining room, washer/dryer in unit, front and back patio with patio furniture. The home has a driveway so parking is hassle-free! Very quiet and safe neighborhood.

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!

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!

The Creekside Cottage: Downtown | Pet-Friendly

Welcome to the Creekside Cottage, a 2 bedroom/1.5 bathroom spacious home, offering a secluded escape by the creek yet just a short stroll through the gardens of Shepherdstown to shopping and dining. Perfect for getaways, family visits, or university stays, this Creekside Cottage offers a roomy interior, cozy living room, modern kitchen, fire pit, and a private patio & porch to be enjoyed along the Town Run.

The GW Hollida Cottage of Shepherdstown

Let time slow just a bit at this unique and tranquil getaway! This recently renovated cottage is situated just behind the GW Hollida house, circa early 1800s. Whether taking a few extra breaths of fresh air on the deck, taking a stroll through the 5 acres of serenity, or kicking back to enjoy some peace and quiet, we are confident you'll love this place as much as we do!