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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, 386 reviews
Top guest favourite
Treehouse in Shepherdstown
Cozy West Virginia Treehouse
2 beds
12–17 Jul
4.97 out of 5 average rating, 422 reviews
Top guest favourite
Cottage in Shepherdstown
The Creekside Cottage: Downtown | Pet-Friendly
2 bedrooms, 3 beds
13–18 Aug
5.0 out of 5 average rating, 178 reviews
Guest favourite
Flat in Shepherdstown
Charming Studio Apt on German St
1 queen bed
5–10 Jul
4.92 out of 5 average rating, 280 reviews
Top guest favourite
Flat in Shepherdstown
The 1763 House - Stay in Downtown Shepherdstown
1 bedroom, 1 queen bed
5–10 Jul
4.97 out of 5 average rating, 269 reviews
Top guest favourite
Room in Shepherdstown
Isn’t it romantic? Charming— with all the feels
1 queen bed
4–9 Jul
4.97 out of 5 average rating, 253 reviews
Guest favourite
Flat in Shepherdstown
Downtown: Explore Shepherdstown from cozy 1br apar
1 bedroom, 2 beds
2–7 Aug
4.96 out of 5 average rating, 441 reviews
Top guest favourite
Home in Shepherdstown
LeLe’s Landing: Come take a Scrabble Sabatical
4 bedrooms, 5 beds
30 Jul – 4 Aug
4.96 out of 5 average rating, 57 reviews
Top guest favourite
Cabin in Shepherdstown
The Log Cabin
1 bedroom, 2 beds
14–19 Jul
4.96 out of 5 average rating, 535 reviews
Top guest favourite
Room in Shepherdstown
Idyllic bedroom in peaceful rural setting
2 beds
22–27 Jul
4.97 out of 5 average rating, 202 reviews
Guest favourite
Home in Shepherdstown
Shepherd's Rest
2 bedrooms, 3 beds
12–17 Jul
5.0 out of 5 average rating, 5 reviews
Guest favourite
Flat in Shepherdstown
Downtown Modern 2BR step from dining and shopping
2 bedrooms, 2 beds
5–10 Jul
4.94 out of 5 average rating, 184 reviews
Top guest favourite
Cottage in Shepherdstown
NEW * The Getaway Cottage at Rocky Marsh Farm
2 bedrooms, 2 queen beds
3–8 Aug
4.97 out of 5 average rating, 210 reviews
Top guest favourite
Guest suite in Shepherdstown
Historic Scrabble, Shepherdstown
1 bedroom, 1 king bed
7–12 Sept
4.96 out of 5 average rating, 745 reviews
Guest favourite
Home in Shepherdstown
Exclusive Wooded Chalet w Magnificent River Views
4 bedrooms, 5 beds
5–10 Jul
4.96 out of 5 average rating, 92 reviews
Top guest favourite
Tiny home in Shepherdstown
Studio: Downtown Hideaway & Waterside Garden Oasis
1 double bed
24–29 Jul
5.0 out of 5 average rating, 213 reviews
Guest favourite
Flat in Shepherdstown
Downtown Modern Studio apartment | History & Dining steps away
1 bed
19–24 Jul
4.92 out of 5 average rating, 254 reviews
Top guest favourite
Home in Shepherdstown
Comfortable and Large Historic House in Shep
6 bedrooms, 8 beds
3–8 Aug
4.88 out of 5 average rating, 132 reviews
Top guest favourite
Home in Shepherdstown
WV Blue AND Gold (entire property)
4 bedrooms, 9 beds
2–7 Aug
5.0 out of 5 average rating, 11 reviews