Skip to content
Sign up
Log in
Vacation rentals in Shepherdstown

Vacation rentals in Shepherdstown

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Shepherdstown

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

The Little Schoolhouse
SUPERHOST
Entire house · 4 guests · 2 beds · 1 bath

The Little SchoolhouseThe Little Schoolhouse is a charming, 1800’s home that once served as a one-room schoolhouse and is now on the National Historical Registry. Nestled within feet of Rocky Marsh Run this fully remodeled, quaint one-bedroom, one-bathroom home has all of today’s modern conveniences with the charm of the 1800’s. The home is conveniently located 4 miles from downtown Shepherdstown, half a mile from the Potomac River, 5 miles from the C&O Canal and 8 miles from Antietam National Battlefield.

The Cottage At Fairview Farm, An Organic Property
SUPERHOST
Entire cottage · 4 guests · 4 beds · 1.5 baths

The Cottage At Fairview Farm, An Organic PropertySitting atop a hill on 23 acres at historic Fairview Farm, Circa 1737, the newly built cottage is surrounded by pasture, organic gardens, history & overlooks the Harpers Ferry Gap. We are just a few miles from Charles Town, Harpers Ferry, Shepardstown & the Hollywood Casino, the Appalachia trail, the Shenandoah & Potomac Rivers, and many historical sites. Start your day watching the sun rise from the deck and sunsets from the porch. We are taking extra precautions sanitizing between guests...

Cozy West Virginia Treehouse
SUPERHOST
Treehouse · 4 guests · 2 beds · 1 bath

Cozy West Virginia TreehouseThanks 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.

Vacation rentals for every style

Get the amount of space that is right for you

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Shepherdstown vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Shepherdstown

SUPERHOST
  1. Private room
  2. Shepherdstown
Cozy School Bus Conversion

The bus is just a 4 minute drive to Shepherdstown and 15 minute drive to Harpers Ferry. There’s a fire pit near the bus and a wood stove in the bus if you prefer to use it, however the heaters work fine to keep the bus warm. We provide firewood also. There’s an air conditioner for warm days as well. The bathhouse is on the back side of the host’s house and is about a 30 second walk from the bus.

$85 per night
SUPERHOST
  1. Barn
  2. Harpers Ferry
La Soledad Lavender Farm on the Potomac

Brand new studio apartment with private entrance over a detached barn style garage. Situated between our lavender field and view of Potomac River in historic Harper’s Ferry. Walking distance to lower town Harper’s Ferry and Harpers Ferry Historic National Park.

$219 per night
SUPERHOST
  1. Entire apartment
  2. Shepherdstown
Explore Shepherdstown from downtown 1br apt

Come and enjoy a warm, yet modern space just steps away from history, dining, the great outdoors, and Shepherd University campus! This one bedroom apartment offers street front convenience while still providing a clean and private escape from the downtown bustle! This is a perfect place to relax while enjoying historic Shepherdstown!

$106 per night
SUPERHOST
  1. Entire cabin
  2. Shepherdstown
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.

$117 per night
SUPERHOST
  1. Entire cabin
  2. Shepherdstown
Knott Cabin | Woodsy Setting | Near Potomac River

Semi-isolated 1940s cedar-shingled WV cabin with midcentury modern furnishings in peaceful wooded setting. Lovely spot for hanging out or working. Queen bed on main floor. Kitchenette. Fire pit & gas grill. Front porch with rockers. Outdoor patio dining area. River access 0.1 mi for kayaking, canoeing or swimming. Convenient to Shepherdstown & Harpers Ferry. Modern bathroom with tiled walk-in shower, barn door, vessel sink and heated floor. Echo Dot + CD player & CD library.

$125 per night
SUPERHOST
  1. Entire cottage
  2. Shepherdstown
Potomac Cottage/Riverfront (Entire House)

Escape to this tranquil, riverfront retreat with stunning, year-round river views, a private dock (available in Spring and Summer) and firepit. When you get tired of doing absolutely nothing, maybe try some fishing, explore the Potomac, or visit nearby attractions--Shepherdstown, Antietam Battlefield, Crystal Grottoes and numerous vineyards, to name a few. Two kayaks, a canoe, paddles, and lifejackets are available for your use.

$150 per night
SUPERHOST
  1. Tiny house
  2. Shepherdstown
❤️ 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 2.5 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.

$50 per night
SUPERHOST
  1. Entire cottage
  2. Sharpsburg
Lock Keepers Cottage on C&O Canal/Potomac River

Located just steps away from Dam #4 on the C&O Canal / Potomac River. ( C&O mile marker 84.6) Perfect for a getaway or romantic weekend. You can hike/bike the C&O Canal, bring your kayak/canoe, fish or swim in the river. Sit on the porch and listen to the rumble of the water falling over the dam. Local lore is this was the home of a canal lock keeper or the gate house keeper. For history buffs, there was an attemped crossing of Lee's Army here at the dam. NOT A PARTY HOUSE!!

$135 per night
SUPERHOST
  1. Private room
  2. Sharpsburg
Stone Hill Riverfront Cottage/Historic Property

This fabulous stone cottage sits on a hill behind the main house on a secluded, historic farm on the Potomac River, and has one of the prettiest stretches of the C&O Canal possible, a mere three minute walk away. Old growth trees send sunbeams through the trees nearly every afternoon make it a magical place. Guests can rent 2 kayaks for river use and can arrange to search the property for Native American Indian artifacts which abound, as well as just enjoy stunning scenery and tranquility.

$125 per night
SUPERHOST
  1. Entire cottage
  2. Shepherdstown
Cottage at Rockymarsh

Private, wooded setting convenient to all the amenities of Shepherdstown. Our guests agree: this clean, cozy cottage is their best airbnb experience!

$128 per night
SUPERHOST
  1. Entire guest suite
  2. Shepherdstown
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.

$86 per night
SUPERHOST
  1. Entire house
  2. Sharpsburg
Historic C&O Canal House Charmingly Renovated

Our historic C&O Canal house charmingly renovated. The original 1790 log house, with 1857 additions, was recently updated with modern amenities, while retaining its historic charm. Operated since 2019 as a very successful AirBnB (earlier guest reviews did not fully transfer during re-listing). Multiple outdoor venues on the extensive grounds. Property borders the C&O Canal and the towpath, mile marker 81 and Taylors Landing boat launch on the Potomac River (seasonal river views from property).

$132 per night

Nearby destinations