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Search results; Over 1,000 homes in Shepherdstown

Top guest favourite
Flat in Shepherdstown
The 1763 House - Stay in Downtown Shepherdstown
1 bedroom, 1 bed, 1.5 private bathrooms
20–25 Sept
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4.98 out of 5 average rating, 282 reviews
Guest favourite
Treehouse in Shepherdstown
Cozy West Virginia Treehouse
2 beds, 1.5 bathrooms
8–13 Sept
4.98 out of 5 average rating, 448 reviews
Guest favourite
Flat in Shepherdstown
Downtown - 1BR Apartment on E. German St
1 bedroom, 1 queen bed, 1 bathroom
6–11 Sept
4.93 out of 5 average rating, 400 reviews
Top guest favourite
Room in Shepherdstown
Little Big Sky! A cozy bedroom in the country!
1 queen bed, 1 bathroom
4–9 Sept
4.97 out of 5 average rating, 105 reviews
Top guest favourite
Flat in Shepherdstown
Charming Studio Apt on German St
1 queen bed, 1 bathroom
7–12 Sept
4.92 out of 5 average rating, 292 reviews
Top guest favourite
Room in Shepherdstown
Idyllic bedroom in peaceful rural setting
2 beds, 1 bathroom
9–14 Sept
4.97 out of 5 average rating, 216 reviews
Guest favourite
Flat in Shepherdstown
Downtown: Explore Shepherdstown from cozy 1br apar
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.96 out of 5 average rating, 458 reviews
Guest favourite
Flat in Shepherdstown
Downtown Modern Studio apartment | History & Dining steps away
1 bed, 1 bathroom
12–17 Sept
4.92 out of 5 average rating, 270 reviews
Top guest favourite
Cottage in Shepherdstown
The Creekside Cottage: Downtown | Pet-Friendly
2 bedrooms, 3 beds, 1.5 bathrooms
2–7 Nov
5.0 out of 5 average rating, 196 reviews
Top guest favourite
Guest suite in Shepherdstown
Historic Scrabble, Shepherdstown
1 bedroom, 1 king bed, 1 bathroom
19–24 Sept
4.96 out of 5 average rating, 759 reviews
Guest favourite
Flat in Shepherdstown
Downtown Modern 2BR step from dining and shopping
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.94 out of 5 average rating, 196 reviews
Top guest favourite
Tiny home in Shepherdstown
Studio: Downtown Hideaway & Waterside Garden Oasis
1 double bed, 1 bathroom
4–9 Oct
4.99 out of 5 average rating, 228 reviews
Top guest favourite
Cottage in Shepherdstown
The GW Hollida Cottage of Shepherdstown
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.93 out of 5 average rating, 357 reviews
Top guest favourite
Cabin in Shepherdstown
The Log Cabin
1 bedroom, 2 beds, 1 bathroom
30 Oct – 4 Nov
4.96 out of 5 average rating, 542 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, 270 reviews
Top guest favourite
Cottage in Shepherdstown
NEW * The Getaway Cottage at Rocky Marsh Farm
2 bedrooms, 2 queen beds, 2 bathrooms
8–13 Sept
4.97 out of 5 average rating, 224 reviews
Top guest favourite
Home in Shepherdstown
Welcome to our cute and cozy rocky garden cabin.
1 bedroom, 1 queen bed, 1 bathroom
15–20 Sept
4.96 out of 5 average rating, 91 reviews
Guest favourite
Home in Shepherdstown
Shepherdstown Farmhouse Retreat - 3br/2bath
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.81 out of 5 average rating, 37 reviews
Top guest favourite
Home in Shepherdstown
Comfortable and Large Historic House in Shep
6 bedrooms, 8 beds, 4 bathrooms
10–15 Sept
4.88 out of 5 average rating, 137 reviews