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Search results; Over 1,000 homes in Shepherdstown

Top guest favourite
Guest suite in Shepherdstown
Historic Scrabble, Shepherdstown
1 bedroom, 1 bed, 1 private bathroom
14–19 Sept
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4.96 out of 5 average rating, 758 reviews
Top guest favourite
Treehouse in Shepherdstown
Cozy West Virginia Treehouse
2 beds, 1.5 bathrooms
25–30 Aug
4.98 out of 5 average rating, 441 reviews
Guest favourite
Flat in Shepherdstown
Downtown: Explore Shepherdstown from cozy 1br apar
1 bedroom, 2 beds, 1 bathroom
17–22 Aug
4.96 out of 5 average rating, 453 reviews
Top guest favourite
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, 190 reviews
Guest favourite
Flat in Shepherdstown
Downtown - 1BR Apartment on E. German St
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.93 out of 5 average rating, 393 reviews
Top guest favourite
Cottage in Shepherdstown
NEW * The Getaway Cottage at Rocky Marsh Farm
2 bedrooms, 2 queen beds, 2 bathrooms
7–12 Sept
4.97 out of 5 average rating, 222 reviews
Guest favourite
Flat in Shepherdstown
Downtown Modern Studio apartment | History & Dining steps away
1 bed, 1 bathroom
16–21 Aug
4.92 out of 5 average rating, 264 reviews
Top guest favourite
Cabin in Shepherdstown
The Log Cabin
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.96 out of 5 average rating, 539 reviews
Top guest favourite
Tiny home in Shepherdstown
Studio: Downtown Hideaway & Waterside Garden Oasis
1 double bed, 1 bathroom
16–21 Aug
4.99 out of 5 average rating, 225 reviews
Top guest favourite
Room in Shepherdstown
Isn’t it romantic? Charming— with all the feels
1 queen bed, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 267 reviews
Top guest favourite
Room in Shepherdstown
Little Big Sky! A cozy bedroom in the country!
1 queen bed, 1 bathroom
15–20 Aug
4.97 out of 5 average rating, 100 reviews
Guest favourite
Cottage in Shepherdstown
Charming and cozy, walk to town
1 bedroom, 2 beds, 1 bathroom
17–22 Aug
4.85 out of 5 average rating, 13 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
Charming Studio Apt on German St
1 queen bed, 1 bathroom
16–21 Aug
4.92 out of 5 average rating, 287 reviews
Top guest favourite
Cottage in Shepherdstown
The GW Hollida Cottage of Shepherdstown
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.93 out of 5 average rating, 350 reviews
Top guest favourite
Flat in Shepherdstown
The 1763 House - Stay in Downtown Shepherdstown
1 bedroom, 1 queen bed, 1.5 bathrooms
20–25 Sept
4.97 out of 5 average rating, 277 reviews
Guest favourite
Home in Shepherdstown
Exclusive Wooded Chalet w Magnificent River Views
4 bedrooms, 5 beds, 3.5 bathrooms
1–6 Sept
4.96 out of 5 average rating, 97 reviews
Home in Bolivar
Cozy Getaway Near History, Hiking & Adventure
3 bedrooms, 5 beds, 2 bathrooms
29 Aug – 3 Sept
New place to stay
Guest favourite
Home in Shepherdstown
Shepherdstown Farmhouse Retreat - 3br/2bath
3 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
4.81 out of 5 average rating, 36 reviews