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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
6–11 Sept
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4.91 out of 5 average rating, 306 reviews
Top guest favourite
Tiny home in Shepherdstown
Studio: Downtown Hideaway & Waterside Garden Oasis
5.0 out of 5 average rating, 220 reviews, 1 bed, 1 bathroom
9–14 Aug
Guest favourite
Flat in Shepherdstown
Downtown: Explore Shepherdstown from cozy 1br apar
4.96 out of 5 average rating, 449 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Room in Shepherdstown
Isn’t it romantic? Charming— with all the feels
4.97 out of 5 average rating, 262 reviews, 1 queen bed, 1 bathroom
9–14 Aug
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Treehouse in Shepherdstown
Cozy West Virginia Treehouse
4.97 out of 5 average rating, 437 reviews, 2 beds, 1.5 bathrooms
5–10 Aug
Top guest favourite
Flat in Shepherdstown
The 1763 House - Stay in Downtown Shepherdstown
4.97 out of 5 average rating, 273 reviews, 1 bedroom, 1 bed, 1.5 bathrooms
9–14 Aug
Top guest favourite
Cabin in Shepherdstown
The Log Cabin
4.96 out of 5 average rating, 535 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Room in Shepherdstown
Little Big Sky! A cozy bedroom in the country!
4.97 out of 5 average rating, 100 reviews, 1 queen bed, 1 bathroom
8–13 Aug
Guest favourite
Flat in Shepherdstown
Downtown Modern Studio apartment | History & Dining steps away
4.92 out of 5 average rating, 258 reviews, 1 bed, 1 bathroom
2–7 Aug
Guest favourite
Flat in Shepherdstown
Downtown - 1BR Apartment on E. German St
4.93 out of 5 average rating, 390 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Guest favourite
Flat in Shepherdstown
Charming Studio Apt on German St
4.92 out of 5 average rating, 285 reviews, 1 bed, 1 bathroom
2–7 Aug
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Room in Shepherdstown
Idyllic bedroom in peaceful rural setting
4.97 out of 5 average rating, 209 reviews, 2 beds, 1 bathroom
5–10 Aug
Top guest favourite
Cottage in Shepherdstown
The GW Hollida Cottage of Shepherdstown
4.93 out of 5 average rating, 344 reviews, 1 bedroom, 1 bed, 1 bathroom
3–8 Aug
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Cottage in Shepherdstown
The Creekside Cottage: Downtown | Pet-Friendly
5.0 out of 5 average rating, 185 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
30 Aug – 4 Sept
Guest favourite
Flat in Shepherdstown
Downtown Modern 2BR step from dining and shopping
4.94 out of 5 average rating, 187 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
Guest favourite
Home in Shepherdstown
Shepherd's Rest
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
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Room in Sharpsburg
Hidden Gem #1 - Stay with Dan and Alice.
4.97 out of 5 average rating, 183 reviews, 1 bed, 1 bathroom
2–7 Aug
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Cottage in Shepherdstown
NEW * The Getaway Cottage at Rocky Marsh Farm
4.97 out of 5 average rating, 215 reviews, 2 bedrooms, 2 beds, 2 bathrooms
9–14 Aug
Top guest favourite
Tiny home in Shepherdstown
Cozy School Bus Conversion
4.97 out of 5 average rating, 992 reviews, 1 bedroom, 1 bed, No bathroom
1–6 Apr