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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
19–24 Sept
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4.95 out of 5 average rating, 755 reviews
Top guest favourite
Treehouse in Shepherdstown
Cozy West Virginia Treehouse
2 beds
25–30 Aug
4.97 out of 5 average rating, 437 reviews
Guest favourite
Flat in Shepherdstown
Downtown: Explore Shepherdstown from cozy 1br apar
1 bedroom, 2 beds
17–22 Aug
4.96 out of 5 average rating, 452 reviews
Guest favourite
Flat in Shepherdstown
Downtown - 1BR Apartment on E. German St
1 bedroom, 1 queen bed
7–12 Aug
4.93 out of 5 average rating, 391 reviews
Top guest favourite
Cottage in Shepherdstown
The Creekside Cottage: Downtown | Pet-Friendly
2 bedrooms, 3 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 189 reviews
Top guest favourite
Cabin in Shepherdstown
The Log Cabin
1 bedroom, 2 beds
6–11 Aug
4.96 out of 5 average rating, 537 reviews
Top guest favourite
Cottage in Shepherdstown
NEW * The Getaway Cottage at Rocky Marsh Farm
2 bedrooms, 2 queen beds
9–14 Aug
4.97 out of 5 average rating, 219 reviews
Top guest favourite
Home in Shepherdstown
LeLe’s Landing: Come take a Scrabble Sabatical
4 bedrooms, 5 beds
25–30 Aug
4.96 out of 5 average rating, 57 reviews
Top guest favourite
Flat in Shepherdstown
The 1763 House - Stay in Downtown Shepherdstown
1 bedroom, 1 queen bed
9–14 Aug
4.97 out of 5 average rating, 275 reviews
Guest favourite
Flat in Shepherdstown
Downtown Modern Studio apartment | History & Dining steps away
1 bed
3–8 Aug
4.92 out of 5 average rating, 259 reviews
Guest favourite
Cottage in Shepherdstown
Charming and cozy, walk to town
1 bedroom, 2 beds
3–8 Aug
4.83 out of 5 average rating, 12 reviews
Top guest favourite
Tiny home in Shepherdstown
Studio: Downtown Hideaway & Waterside Garden Oasis
1 double bed
9–14 Aug
5.0 out of 5 average rating, 224 reviews
Top guest favourite
Room in Shepherdstown
Isn’t it romantic? Charming— with all the feels
1 queen bed
9–14 Aug
4.97 out of 5 average rating, 265 reviews
Guest favourite
Flat in Shepherdstown
Downtown Modern 2BR step from dining and shopping
2 bedrooms, 2 beds
23–28 Aug
4.94 out of 5 average rating, 193 reviews
Guest favourite
Flat in Shepherdstown
Charming Studio Apt on German St
1 queen bed
3–8 Aug
4.92 out of 5 average rating, 287 reviews
Top guest favourite
Home in Shepherdstown
Shepherd's Rest
2 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Room in Shepherdstown
Idyllic bedroom in peaceful rural setting
2 beds
6–11 Sept
4.97 out of 5 average rating, 212 reviews
Top guest favourite
Cottage in Shepherdstown
The GW Hollida Cottage of Shepherdstown
1 bedroom, 1 queen bed
20–25 Aug
4.93 out of 5 average rating, 347 reviews
Guest favourite
Home in Shepherdstown
Exclusive Wooded Chalet w Magnificent River Views
4 bedrooms, 5 beds
1–6 Sept
4.96 out of 5 average rating, 96 reviews