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Search results; Over 1,000 homes in Shepherdstown

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Top guest favourite
Tiny home in Shepherdstown
Cozy School Bus Conversion
1 bedroom, 1 bed, No bathroom
1–6 Apr
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4.97 out of 5 average rating, 992 reviews
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Flat in Shepherdstown
Downtown - 1BR Apartment on E. German St
1 bedroom, 1 queen bed, 1 bathroom
18–23 Oct
4.93 out of 5 average rating, 403 reviews
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Flat in Shepherdstown
Charming Studio Apt on German St
1 queen bed, 1 bathroom
18–23 Oct
4.92 out of 5 average rating, 293 reviews
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Top guest favourite
Flat in Shepherdstown
The 1763 House - Stay in Downtown Shepherdstown
1 bedroom, 1 queen bed, 1.5 bathrooms
12–17 Oct
4.98 out of 5 average rating, 286 reviews
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Flat in Shepherdstown
Downtown: Explore Shepherdstown from cozy 1br apar
1 bedroom, 2 beds, 1 bathroom
11–16 Oct
4.96 out of 5 average rating, 463 reviews
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Guest favourite
Treehouse in Shepherdstown
Cozy West Virginia Treehouse
2 beds, 1.5 bathrooms
14–19 Nov
4.97 out of 5 average rating, 456 reviews
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Home in Shepherdstown
Charming Shepherdstown Home - Walk to Downtown
3 bedrooms, 3 beds, 1 bathroom
24–29 Oct
New place to stay
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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, 203 reviews
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Flat in Shepherdstown
Downtown Modern 2BR step from dining and shopping
2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
4.93 out of 5 average rating, 198 reviews
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Flat in Shepherdstown
Downtown Modern Studio apartment | History & Dining steps away
1 bed, 1 bathroom
11–16 Oct
4.92 out of 5 average rating, 273 reviews
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Home in Shepherdstown
Small Town Living: Historic District Guesthouse
3 bedrooms, 5 beds, 2 bathrooms
8–13 Nov
4.96 out of 5 average rating, 304 reviews
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Home in Shepherdstown
Shepherdstown Farmhouse Retreat - 3br/2bath
3 bedrooms, 3 beds, 2 bathrooms
18–23 Oct
4.81 out of 5 average rating, 37 reviews
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Room in Shepherdstown
Isn’t it romantic? Charming— with all the feels
1 queen bed, 1 bathroom
25–30 Oct
4.97 out of 5 average rating, 270 reviews
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Guest suite in Shepherdstown
Historic Scrabble, Shepherdstown
1 bedroom, 1 king bed, 1 bathroom
14–19 Nov
4.96 out of 5 average rating, 763 reviews
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Room in Shepherdstown
Idyllic bedroom in peaceful rural setting
2 beds, 1 bathroom
1–6 Nov
4.97 out of 5 average rating, 221 reviews
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Cottage in Shepherdstown
NEW * The Getaway Cottage at Rocky Marsh Farm
2 bedrooms, 2 queen beds, 2 bathrooms
4–9 Oct
4.97 out of 5 average rating, 227 reviews
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Top guest favourite
Cabin in Shepherdstown
The Log Cabin
1 bedroom, 2 beds, 1 bathroom
1–6 Nov
4.96 out of 5 average rating, 548 reviews
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Home in Shepherdstown
Comfortable and Large Historic House in Shep
6 bedrooms, 8 beds, 4 bathrooms
27 Oct – 1 Nov
4.88 out of 5 average rating, 137 reviews
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Top guest favourite
Home in Shepherdstown
LeLe’s Landing: Come take a Scrabble Sabatical
4 bedrooms, 5 beds, 2.5 bathrooms
13–18 Nov
4.97 out of 5 average rating, 59 reviews