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Search results; Over 1,000 homes in Shepherdstown

Guest favourite
Cottage in Shepherdstown
Riverfront Cottage in Shepherdstown, WV
2 bedrooms, 3 beds, 2 private bathrooms
27 Aug – 1 Sept
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4.91 out of 5 average rating, 304 reviews
Top guest favourite
Treehouse in Shepherdstown
Cozy West Virginia Treehouse
2 beds, 1.5 bathrooms
25–30 Aug
4.97 out of 5 average rating, 429 reviews
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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, 444 reviews
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Room in Shepherdstown
Isn’t it romantic? Charming— with all the feels
1 queen bed, 1 bathroom
21–26 Jul
4.97 out of 5 average rating, 260 reviews
Guest favourite
Flat in Shepherdstown
Downtown - 1BR Apartment on E. German St
1 bedroom, 1 queen bed, 1 bathroom
2–7 Aug
4.93 out of 5 average rating, 388 reviews
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Cottage in Shepherdstown
The Creekside Cottage: Downtown | Pet-Friendly
2 bedrooms, 3 beds, 1.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 183 reviews
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Cabin in Shepherdstown
The Log Cabin
1 bedroom, 2 beds, 1 bathroom
26–31 Jul
4.96 out of 5 average rating, 535 reviews
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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, 212 reviews
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Room in Shepherdstown
Idyllic bedroom in peaceful rural setting
2 beds, 1 bathroom
22–27 Jul
4.97 out of 5 average rating, 206 reviews
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Flat in Shepherdstown
The 1763 House - Stay in Downtown Shepherdstown
1 bedroom, 1 queen bed, 1.5 bathrooms
2–7 Aug
4.97 out of 5 average rating, 271 reviews
Top guest favourite
Home in Shepherdstown
LeLe’s Landing: Come take a Scrabble Sabatical
4 bedrooms, 5 beds, 2.5 bathrooms
25–30 Aug
4.96 out of 5 average rating, 57 reviews
Guest favourite
Flat in Shepherdstown
Downtown Modern Studio apartment | History & Dining steps away
1 bed, 1 bathroom
2–7 Aug
4.92 out of 5 average rating, 255 reviews
Top guest favourite
Cottage in Shepherdstown
The GW Hollida Cottage of Shepherdstown
1 bedroom, 1 queen bed, 1 bathroom
19–24 Jul
4.93 out of 5 average rating, 343 reviews
Guest favourite
Flat in Shepherdstown
Charming Studio Apt on German St
1 queen bed, 1 bathroom
2–7 Aug
4.92 out of 5 average rating, 283 reviews
Guest favourite
Home in Shepherdstown
Shepherd's Rest
2 bedrooms, 3 beds, 2 bathrooms
1–6 Aug
5.0 out of 5 average rating, 7 reviews
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Tiny home in Shepherdstown
Studio: Downtown Hideaway & Waterside Garden Oasis
1 double bed, 1 bathroom
7–12 Aug
5.0 out of 5 average rating, 214 reviews
Guest favourite
Home in Shepherdstown
Exclusive Wooded Chalet w Magnificent River Views
4 bedrooms, 5 beds, 3.5 bathrooms
28 Aug – 2 Sept
4.96 out of 5 average rating, 93 reviews
Guest favourite
Flat in Shepherdstown
Downtown Modern 2BR step from dining and shopping
2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
4.94 out of 5 average rating, 185 reviews
Guest favourite
Home in Shepherdstown
Shepherdstown Farmhouse Retreat - 3br/2bath
3 bedrooms, 3 beds, 2 bathrooms
31 Jul – 5 Aug
4.79 out of 5 average rating, 33 reviews