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Search results; Over 1,000 homes in Shepherdstown

Top guest favourite
Treehouse in Shepherdstown
Cozy West Virginia Treehouse
2 beds, 1.5 private bathrooms
14–19 Jul
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4.97 out of 5 average rating, 429 reviews
Top guest favourite
Room in Shepherdstown
Idyllic bedroom in peaceful rural setting
4.97 out of 5 average rating, 203 reviews, 2 beds, 1 bathroom
22–27 Jul
Top guest favourite
Room in Shepherdstown
Isn’t it romantic? Charming— with all the feels
4.97 out of 5 average rating, 257 reviews, 1 queen bed, 1 bathroom
13–18 Jul
Guest favourite
Flat in Shepherdstown
Charming Studio Apt on German St
4.92 out of 5 average rating, 282 reviews, 1 bed, 1 bathroom
30 Jul – 4 Aug
Guest favourite
Flat in Shepherdstown
Downtown - 1BR Apartment on E. German St
4.93 out of 5 average rating, 387 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Top guest favourite
Cottage in Shepherdstown
The Creekside Cottage: Downtown | Pet-Friendly
5.0 out of 5 average rating, 180 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
30 Aug – 4 Sept
Guest favourite
Home in Shepherdstown
Shepherd's Rest
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
Top guest favourite
Cabin in Shepherdstown
The Log Cabin
4.96 out of 5 average rating, 535 reviews, 1 bedroom, 2 beds, 1 bathroom
14–19 Jul
Guest favourite
Flat in Shepherdstown
Downtown: Explore Shepherdstown from cozy 1br apar
4.96 out of 5 average rating, 441 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Flat in Shepherdstown
The 1763 House - Stay in Downtown Shepherdstown
4.97 out of 5 average rating, 270 reviews, 1 bedroom, 1 bed, 1.5 bathrooms
2–7 Aug
Guest favourite
Flat in Shepherdstown
Downtown Modern 2BR step from dining and shopping
4.94 out of 5 average rating, 184 reviews, 2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
Top guest favourite
Home in Shepherdstown
LeLe’s Landing: Come take a Scrabble Sabatical
4.96 out of 5 average rating, 57 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
25–30 Aug
Guest favourite
Flat in Shepherdstown
Downtown Modern Studio apartment | History & Dining steps away
4.92 out of 5 average rating, 254 reviews, 1 bed, 1 bathroom
2–7 Aug
Guest favourite
Home in Shepherdstown
Shepherdstown Farmhouse Retreat - 3br/2bath
4.78 out of 5 average rating, 32 reviews, 3 bedrooms, 3 beds, 2 bathrooms
31 Jul – 5 Aug
Top guest favourite
Home in Shepherdstown
Comfortable and Large Historic House in Shep
4.88 out of 5 average rating, 133 reviews, 6 bedrooms, 8 beds, 4 bathrooms
3–8 Aug
Top guest favourite
Cottage in Shepherdstown
NEW * The Getaway Cottage at Rocky Marsh Farm
4.97 out of 5 average rating, 210 reviews, 2 bedrooms, 2 beds, 2 bathrooms
3–8 Aug
Top guest favourite
Guest suite in Shepherdstown
Historic Scrabble, Shepherdstown
4.96 out of 5 average rating, 746 reviews, 1 bedroom, 1 bed, 1 bathroom
13–18 Oct
Guest favourite
Home in Shepherdstown
Exclusive Wooded Chalet w Magnificent River Views
4.96 out of 5 average rating, 93 reviews, 4 bedrooms, 5 beds, 3.5 bathrooms
28 Aug – 2 Sept
Top guest favourite
Home in Shepherdstown
Small Town Living: Historic District Guesthouse
4.96 out of 5 average rating, 292 reviews, 3 bedrooms, 5 beds, 2 bathrooms
16–21 Aug