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Guest favorite
Home in Shepherdstown
LeLe’s Landing: Come take a Scrabble Sabatical
8 guests4 bedrooms5 beds2.5 baths
Jul 13 – 18
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Jul 13 – 18
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R25,369 ZAR for 5 nights

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Top guest favorite
Room in Shepherdstown
Stay with SharonCasual homemaker!,
Little Big Sky! A cozy bedroom in the country!
Jul 17 – 22
R5,307 ZAR for 5 nights
4.97 out of 5 average rating, 71 reviews
Top guest favorite
Room in Shepherdstown
Stay with Donna
Isn’t it romantic? Charming— with all the feels
Aug 2 – 7
R5,550 ZAR for 5 nights
4.97 out of 5 average rating, 189 reviews
Top guest favorite
Apartment in Shepherdstown
Downtown: Explore Shepherdstown from cozy 1br apar
1 bed
Aug 2 – 7
R13,848 ZAR for 5 nights
4.96 out of 5 average rating, 360 reviews
Top guest favorite
Tiny home in Shepherdstown
Studio: Downtown Hideaway & Waterside Garden Oasis
1 double bed
Aug 15 – 20
R17,040 ZAR for 5 nights
4.99 out of 5 average rating, 152 reviews
Top guest favorite
Cottage in Shepherdstown
The Creekside Cottage: Downtown | Pet-Friendly
2 beds
Aug 24 – 29
R25,581 ZAR for 5 nights
5.0 out of 5 average rating, 107 reviews
Guest favorite
Apartment in Shepherdstown
New - Loft Studio in Historic Shepherdstown
1 queen bed
Aug 3 – 8
R14,905 ZAR for 5 nights
4.94 out of 5 average rating, 100 reviews
Top guest favorite
Cabin in Shepherdstown
The Log Cabin
2 beds
Jul 18 – 23
R15,116 ZAR for 5 nights
4.95 out of 5 average rating, 480 reviews
Top guest favorite
Room in Sharpsburg
Stay with DanielCommerical millwork,
Hidden Gem - Stay with Dan and Alice.
Jul 24 – 29
R4,948 ZAR for 5 nights
4.96 out of 5 average rating, 119 reviews
Top guest favorite
Tiny home in Shepherdstown
Cozy School Bus Conversion
1 double bed
Jul 9 – 14
R10,381 ZAR for 5 nights
4.97 out of 5 average rating, 968 reviews
Top guest favorite
Treehouse in Shepherdstown
Cozy West Virginia Treehouse
2 beds
Jul 18 – 23
R20,423 ZAR for 5 nights
4.97 out of 5 average rating, 345 reviews
Top guest favorite
Apartment in Shepherdstown
The 1763 House - Stay in Downtown Shepherdstown
1 bed
Jul 25 – 30
R19,239 ZAR for 5 nights
4.97 out of 5 average rating, 192 reviews
Top guest favorite
Guest suite in Shepherdstown
Historic Scrabble, Shepherdstown
1 king bed
Aug 21 – 26
R9,831 ZAR for 5 nights
4.96 out of 5 average rating, 669 reviews
Guest favorite
Cottage in Shepherdstown
The GW Hollida Cottage of Shepherdstown
1 queen bed
Jul 20 – 25
R11,480 ZAR for 5 nights
4.93 out of 5 average rating, 290 reviews
Guest favorite
Apartment in Shepherdstown
1 Bedroom Apt in Historic Downtown Shepherdstown
1 queen bed
Aug 10 – 15
R14,905 ZAR for 5 nights
4.93 out of 5 average rating, 336 reviews
Superhost
Cottage in Shepherdstown
Riverfront Cottage in Shepherdstown, WV
3 beds
Aug 2 – 7
R23,023 ZAR for 5 nights
4.9 out of 5 average rating, 275 reviews
Top guest favorite
Cottage in Shepherdstown
NEW * The Getaway Cottage at Rocky Marsh Farm
2 beds
Jul 13 – 18
R24,947 ZAR for 5 nights
4.97 out of 5 average rating, 158 reviews
Guest favorite
Apartment in Shepherdstown
Charming Studio Apt in Downtown Shepherdstown
1 queen bed
Aug 1 – 6
R13,953 ZAR for 5 nights
4.92 out of 5 average rating, 249 reviews
Top guest favorite
Home in Shepherdstown
Small Town Living: Historic District Guesthouse
5 beds
Aug 17 – 22
R24,207 ZAR for 5 nights
4.95 out of 5 average rating, 256 reviews