Vacation rentals in Shepherdstown

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Top-rated vacation rentals in Shepherdstown

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

Guest favorite

Guest suite in Shepherdstown

4.96 out of 5 average rating, 563 reviews

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.

Jun 27 – Jul 4

R1,761 ZAR per night
Guest favorite

Guest suite in Shepherdstown

4.99 out of 5 average rating, 205 reviews

Private Suite in Shepherdstown WV

Your sun-drenched suite awaits in my serene bungalow! Self check-in with keypad lock through your separate driveway and entrance. Free parking in front. Private porch with seating and table overlooking the garden. Walk downtown in five minutes to all that Shepherdstown has to offer - Shepherd University, restaurants, shopping, pubs, and theatre. Close by- the C&O Canal Towpath, Potomac River, Harper's Ferry, and Antietam National Battlefields. Bikers, hikers, and kayakers especially welcome!

Jun 10 – 17

R1,880 ZAR per night
Guest favorite

Cottage in Shepherdstown

4.9 out of 5 average rating, 224 reviews

Riverfront Cottage in Shepherdstown, WV

Escape to this tranquil, riverfront retreat with stunning, year-round river views, a private dock (available late May-Sept) & firepit. Relax, fish, explore, or visit nearby attractions in Shepherdstown, Sharpsburg, & Harper's Ferry. Two kayaks, a canoe, paddles, & lifejackets are available for your use. All water activities are at your own risk. WV DNR requires all boaters to have a lifejacket and all boats to have a whistle. Please bring your own whistle(s). MD or WV fishing license is fine.

Jun 17 – 24

R3,931 ZAR per night

Popular amenities for Shepherdstown vacation rentals

Stay near Shepherdstown's top sights

Bavarian Inn, Resort and Brewing Company47 locals recommend
Blue Moon Cafe47 locals recommend
Maria's Taqueria23 locals recommend
Betty's Restaurant17 locals recommend
The Green Pineapple10 locals recommend
Shepherdstown Sweet Shop Bakery12 locals recommend

Other great vacation rentals in Shepherdstown

Guest favorite

Guest suite in Sharpsburg

4.99 out of 5 average rating, 166 reviews

The River Bend Retreat ~ C&O Canal ~ Antietam

Jul 2 – 9

R2,516 ZAR per night
Guest favorite

Home in Bolivar

4.96 out of 5 average rating, 178 reviews

Newly renovated - Walk to Harpers Ferry NP

Dec 7 – 14

R2,162 ZAR per night
Guest favorite

Guest suite in Harpers Ferry

4.98 out of 5 average rating, 500 reviews

Beautiful suite, spa bathroom & gardens

Dec 30 – Jan 6

R2,750 ZAR per night
Superhost

Home in Shepherdstown

4.79 out of 5 average rating, 126 reviews

Plum Lazy on the Potomac

Sep 18 – 25

R3,543 ZAR per night
Guest favorite

Apartment in Harpers Ferry

4.99 out of 5 average rating, 360 reviews

Taylor Den

Jun 10 – 17

R1,830 ZAR per night
Superhost

Loft in Martinsburg

4.9 out of 5 average rating, 108 reviews

The Penthouse-Cool Vibes

Nov 4 – 11

R2,504 ZAR per night
Guest favorite

Cottage in Sharpsburg

4.95 out of 5 average rating, 151 reviews

Lock Keepers Cottage on C&O Canal/Potomac River

Jun 15 – 22

R3,403 ZAR per night
Guest favorite

Guest suite in Smithsburg

4.99 out of 5 average rating, 146 reviews

Creekside Retreat at the Jewel Vinsota

Sep 17 – 24

R1,637 ZAR per night
Guest favorite

Apartment in Charles Town

4.96 out of 5 average rating, 476 reviews

Private efficiency apartment

Dec 25 – Jan 1

R1,556 ZAR per night
Guest favorite

Cabin in Myersville

4.97 out of 5 average rating, 247 reviews

Cabin on Middle Creek - Myersville MD - Middletown

Mar 19 – 26

R2,147 ZAR per night
Guest favorite

Tiny home in Shepherdstown

5.0 out of 5 average rating, 57 reviews

Studio: Downtown Hideaway & Waterside Garden Oasis

Jul 1 – 8

R2,794 ZAR per night
Superhost

Cottage in Shepherdstown

4.93 out of 5 average rating, 73 reviews

Cottage on Ray

Aug 20 – 27

R2,542 ZAR per night

Quick stats about vacation rentals in Shepherdstown

Total rentals

20 properties

Wifi availability

20 properties include access to wifi

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

2K reviews

Nightly prices starting at

R1,704 ZAR before taxes and fees

Destinations to explore