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Search results; Over 1,000 homes in Boonsboro

Top guest favourite
Chalet in Boonsboro
Mountain Myst
3 bedrooms, 4 beds, 2.5 shared bathrooms
8–13 Sept
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4.94 out of 5 average rating, 615 reviews
Guest favourite
Home in Boonsboro
Charming 1800s House in the Town of Boonsboro
3 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Boonsboro
46 South Main Suite #1
1 bedroom, 2 beds, 1 bathroom
2–7 Oct
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Boonsboro
The Overlook~ Exquisite Views
3 bedrooms, 4 beds, 2.5 bathrooms
22–27 Aug
4.92 out of 5 average rating, 51 reviews
Top guest favourite
Cabin in Boonsboro
Little Lodge
2 bedrooms, 3 beds, 1 bathroom
21–26 Sept
4.95 out of 5 average rating, 446 reviews
Guest favourite
Flat in Boonsboro
The Corner House-1 BR Apt
1 bedroom, 2 beds, 1 bathroom
20–27 Aug
5.0 out of 5 average rating, 36 reviews
Top guest favourite
Room in Sharpsburg
Hidden Gem #1 - Stay with Dan and Alice.
1 bed, 1 bathroom
25–30 Aug
4.97 out of 5 average rating, 185 reviews
Top guest favourite
Guest house in Smithsburg
Jewel Vinsota Artist's Guesthouse
1 bedroom, 1 double bed, 1 bathroom
19–24 Sept
4.97 out of 5 average rating, 854 reviews
Superhost
Home in Myersville
Hillside Haven
3 bedrooms, 5 beds, 1.5 bathrooms
26 Sept – 1 Oct
New place to stay
Top guest favourite
Home in Myersville
The Crooked Cottage: a Cozy, Curated Escape
2 bedrooms, 2 beds, 2 bathrooms
30 Aug – 4 Sept
4.98 out of 5 average rating, 313 reviews
Flat in Hagerstown
Creative Living | A Sculptor’s Home
1 bedroom, 1 queen bed, 1 bathroom
12–17 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Guest suite in Smithsburg
Creekside Retreat at the Jewel Vinsota
1 bedroom, 2 beds, 1 bathroom
31 Aug – 5 Sept
4.97 out of 5 average rating, 391 reviews
Top guest favourite
Cabin in Shepherdstown
The Log Cabin
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.96 out of 5 average rating, 539 reviews
Guest favourite
Guest house in Boonsboro
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
2 bedrooms, 3 beds, 1 bathroom
22–27 Aug
4.85 out of 5 average rating, 48 reviews
Top guest favourite
Room in Shepherdstown
Idyllic bedroom in peaceful rural setting
2 beds, 1 bathroom
6–11 Sept
4.97 out of 5 average rating, 213 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, 267 reviews
Room in Keedysville
Historic Civil War era stone house
2 beds, 1.5 bathrooms
19–24 Aug
4.81 out of 5 average rating, 293 reviews
Top guest favourite
Home in Martinsburg
1900 Newton School-house
1 bed, 1 bathroom
31 Aug – 5 Sept
4.98 out of 5 average rating, 45 reviews
Top guest favourite
Flat in Myersville
Hillside Hideaway
1 bedroom, 4 beds, 1 bathroom
21–26 Aug
4.94 out of 5 average rating, 33 reviews