Search results; Over 1,000 homes in Shepherdstown

Top guest favourite
Treehouse in Shepherdstown
Cozy West Virginia Treehouse
2 beds, 1.5 private bathrooms
25–30 Aug
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4.97 out of 5 average rating, 429 reviews
Top guest favourite
Flat in Shepherdstown
Downtown: Explore Shepherdstown from cozy 1br apar
2 beds
2–7 Aug
4.96 out of 5 average rating, 442 reviews
Guest favourite
Flat in Shepherdstown
Downtown - 1BR Apartment on E. German St
1 queen bed
2–7 Aug
4.93 out of 5 average rating, 388 reviews
Top guest favourite
Cabin in Shepherdstown
The Log Cabin
2 beds
24–29 Jul
4.96 out of 5 average rating, 535 reviews
Top guest favourite
Room in Shepherdstown
Stay with Donna
Idyllic bedroom in peaceful rural setting
22–27 Jul
4.97 out of 5 average rating, 205 reviews
Top guest favourite
Cottage in Shepherdstown
The Creekside Cottage: Downtown | Pet-Friendly
3 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 183 reviews
Top guest favourite
Home in Shepherdstown
LeLe’s Landing: Come take a Scrabble Sabatical
5 beds
25–30 Aug
4.96 out of 5 average rating, 57 reviews
Top guest favourite
Cottage in Shepherdstown
NEW * The Getaway Cottage at Rocky Marsh Farm
2 queen beds
3–8 Aug
4.97 out of 5 average rating, 210 reviews
Top guest favourite
Room in Shepherdstown
Stay with Donna
Isn’t it romantic? Charming— with all the feels
19–24 Jul
4.97 out of 5 average rating, 258 reviews
Guest favourite
Flat in Shepherdstown
Charming Studio Apt on German St
1 queen bed
2–7 Aug
4.92 out of 5 average rating, 282 reviews
Top guest favourite
Flat in Shepherdstown
The 1763 House - Stay in Downtown Shepherdstown
1 queen bed
2–7 Aug
4.97 out of 5 average rating, 271 reviews
Guest favourite
Home in Shepherdstown
Shepherd's Rest
3 beds
1–6 Aug
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Shepherdstown
Exclusive Wooded Chalet w Magnificent River Views
5 beds
28 Aug – 2 Sept
4.96 out of 5 average rating, 93 reviews
Top guest favourite
Tiny home in Shepherdstown
Studio: Downtown Hideaway & Waterside Garden Oasis
1 double bed
7–12 Aug
5.0 out of 5 average rating, 214 reviews
Top guest favourite
Cottage in Shepherdstown
The GW Hollida Cottage of Shepherdstown
1 queen bed
19–24 Jul
4.93 out of 5 average rating, 343 reviews
Guest favourite
Home in Shepherdstown
Shepherdstown Farmhouse Retreat - 3br/2bath
3 beds
31 Jul – 5 Aug
4.79 out of 5 average rating, 33 reviews
Guest favourite
Flat in Shepherdstown
Downtown Modern Studio apartment | History & Dining steps away
1 bed
2–7 Aug
4.92 out of 5 average rating, 254 reviews
Guest favourite
Flat in Shepherdstown
Downtown Modern 2BR step from dining and shopping
2 beds
2–7 Aug
4.94 out of 5 average rating, 185 reviews
Top guest favourite
Home in Shepherdstown
Comfortable and Large Historic House in Shep
8 beds
3–8 Aug
4.88 out of 5 average rating, 134 reviews