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Search results; Over 1,000 homes in Shepherdstown

Guest favourite
Flat in Shepherdstown
Downtown - 1BR Apartment on E. German St
1 bedroom, 1 bed, 1 private bathroom
2–7 Aug
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4.93 out of 5 average rating, 387 reviews
Top guest favourite
Treehouse in Shepherdstown
Cozy West Virginia Treehouse
2 beds, 1.5 bathrooms
12–17 Jul
4.97 out of 5 average rating, 424 reviews
Top guest favourite
Cottage in Shepherdstown
The Creekside Cottage: Downtown | Pet-Friendly
2 bedrooms, 3 beds, 1.5 bathrooms
13–18 Aug
5.0 out of 5 average rating, 178 reviews
Top guest favourite
Room in Shepherdstown
Isn’t it romantic? Charming— with all the feels
1 queen bed, 1 bathroom
4–9 Jul
4.97 out of 5 average rating, 254 reviews
Guest favourite
Flat in Shepherdstown
Downtown: Explore Shepherdstown from cozy 1br apar
1 bedroom, 2 beds, 1 bathroom
2–7 Aug
4.96 out of 5 average rating, 441 reviews
Guest favourite
Flat in Shepherdstown
Charming Studio Apt on German St
1 queen bed, 1 bathroom
2–7 Jul
4.92 out of 5 average rating, 281 reviews
Top guest favourite
Flat in Shepherdstown
The 1763 House - Stay in Downtown Shepherdstown
1 bedroom, 1 queen bed, 1.5 bathrooms
5–10 Jul
4.97 out of 5 average rating, 269 reviews
Top guest favourite
Home in Shepherdstown
LeLe’s Landing: Come take a Scrabble Sabatical
4 bedrooms, 5 beds, 2.5 bathrooms
30 Jul – 4 Aug
4.96 out of 5 average rating, 57 reviews
Top guest favourite
Room in Shepherdstown
Idyllic bedroom in peaceful rural setting
2 beds, 1 bathroom
22–27 Jul
4.97 out of 5 average rating, 202 reviews
Top guest favourite
Cabin in Shepherdstown
The Log Cabin
1 bedroom, 2 beds, 1 bathroom
14–19 Jul
4.96 out of 5 average rating, 535 reviews
Guest favourite
Flat in Shepherdstown
Downtown Modern 2BR step from dining and shopping
2 bedrooms, 2 beds, 1 bathroom
5–10 Jul
4.94 out of 5 average rating, 184 reviews
Guest favourite
Home in Shepherdstown
Shepherd's Rest
2 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Shepherdstown
Exclusive Wooded Chalet w Magnificent River Views
4 bedrooms, 5 beds, 3.5 bathrooms
5–10 Jul
4.96 out of 5 average rating, 93 reviews
Top guest favourite
Cottage in Shepherdstown
NEW * The Getaway Cottage at Rocky Marsh Farm
2 bedrooms, 2 queen beds, 2 bathrooms
3–8 Aug
4.97 out of 5 average rating, 210 reviews
Top guest favourite
Tiny home in Shepherdstown
Studio: Downtown Hideaway & Waterside Garden Oasis
1 double bed, 1 bathroom
31 Jul – 5 Aug
5.0 out of 5 average rating, 214 reviews
Top guest favourite
Guest suite in Shepherdstown
Historic Scrabble, Shepherdstown
1 bedroom, 1 king bed, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 745 reviews
Guest favourite
Flat in Shepherdstown
Downtown Modern Studio apartment | History & Dining steps away
1 bed, 1 bathroom
19–24 Jul
4.92 out of 5 average rating, 254 reviews
Top guest favourite
Home in Shepherdstown
WV Blue AND Gold (entire property)
4 bedrooms, 9 beds, 2 bathrooms
2–7 Aug
5.0 out of 5 average rating, 13 reviews
Guest favourite
Cabin in Shepherdstown
Charming Cabin in the Woods with River Access
2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
4.91 out of 5 average rating, 78 reviews