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Search results; Over 1,000 homes in Fairplay

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Top guest favourite
Barn in Fairplay
Barn House 1 BR + BIG Loft w/ Queen Bed on 3 Acres
1 bedroom, 2 beds, 1 private bathroom
4–9 Oct
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5.0 out of 5 average rating, 41 reviews
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Home in Boonsboro
Grand 6BR Boonsboro Retreat with Game Room
6 bedrooms, 6 queen beds, 6 bathrooms
23–28 Oct
New place to stay
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Guest favourite
Townhouse in Hagerstown
Classy Chic, KING, Shopping|Dining|Meritus|Hwy 70
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Oct
4.91 out of 5 average rating, 55 reviews
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Superhost
Home in Myersville
Hillside Haven
3 bedrooms, 5 beds, 1.5 bathrooms
5–10 Oct
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Guest favourite
Home in Shepherdstown
Exclusive Wooded Chalet w Magnificent River Views
4 bedrooms, 5 beds, 3.5 bathrooms
4–9 Oct
4.96 out of 5 average rating, 101 reviews
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Guest favourite
Home in Williamsport
Williamsport by the River
3 bedrooms, 4 beds, 2 bathrooms
17–22 Oct
4.81 out of 5 average rating, 37 reviews
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Guest favourite
Cabin in Keedysville
Wingspan Cabin
4 bedrooms, 7 beds, 3 bathrooms
1–6 Oct
4.89 out of 5 average rating, 27 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
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Guest suite in Sharpsburg
Guest Apartment by C & O Canal and Battlefield
2 bedrooms, 2 beds, 1 bathroom
12–17 Oct
4.93 out of 5 average rating, 306 reviews
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Home in Sharpsburg
Charming Historic Canal House C&O Potomac Antietam
2 bedrooms, 3 beds, 1.5 bathrooms
24–29 Oct
4.97 out of 5 average rating, 159 reviews
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Superhost
Townhouse in Hagerstown
*NEW* Elegant Spacious Escape, Serene Wooded Views
4 bedrooms, 5 beds, 3.5 bathrooms
1–6 Oct
4.81 out of 5 average rating, 21 reviews
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Home in Martinsburg
Potomac Hideaway
3 bedrooms, 4 beds, 2 bathrooms
2–7 Oct
New place to stay
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Top guest favourite
Home in Sharpsburg
Restored 1700s Farmhouse with Horse Pasture & Pool
7 bedrooms, 8 beds, 3.5 bathrooms
26–31 Oct
5.0 out of 5 average rating, 47 reviews
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Room in Sharpsburg
Hidden Gem #1 - Stay with Dan and Alice.
1 bed, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 190 reviews
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Guest favourite
Home in Hagerstown
The Palmstead | Stylish 3 BR | Garage EV Charging
3 bedrooms, 3 beds, 2.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 11 reviews
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Top guest favourite
Flat in Myersville
Hillside Hideaway
1 bedroom, 4 beds, 1 bathroom
4–9 Oct
4.95 out of 5 average rating, 37 reviews
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Superhost
Home in Hagerstown
Cozy / Family-Friendly modern home
3 bedrooms, 4 beds, 1.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Home in Hagerstown
Cozy Yellow House
3 bedrooms, 4 beds, 1 bathroom
11–16 Oct
5.0 out of 5 average rating, 87 reviews
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Guest favourite
Home in Martinsburg
The Cozy Haven
3 bedrooms, 3 beds, 2 bathrooms
11–16 Oct
4.93 out of 5 average rating, 142 reviews