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Search results; Over 1,000 homes in Boonsboro

Top guest favourite
Cabin in Boonsboro
Little Lodge
2 bedrooms, 3 beds, 1 private bathroom
14–19 Aug
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4.95 out of 5 average rating, 443 reviews
Guest favourite
Home in Boonsboro
Charming 1800s House in the Town of Boonsboro
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 3 beds, 2 bathrooms
17–22 Aug
Top guest favourite
Home in Boonsboro
The Overlook~ Exquisite Views
4.91 out of 5 average rating, 47 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
19–24 Jul
Top guest favourite
Chalet in Boonsboro
Mountain Myst
4.94 out of 5 average rating, 613 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
31 Aug – 5 Sept
Room in Keedysville
Historic Civil War era stone house
4.81 out of 5 average rating, 293 reviews, 2 beds, 1.5 bathrooms
8–13 Jul
Top guest favourite
Flat in Myersville
Hillside Hideaway
4.94 out of 5 average rating, 31 reviews, 1 bedroom, 4 beds, 1 bathroom
12–17 Jul
Guest favourite
Room in Boonsboro
Dandelion
5.0 out of 5 average rating, 8 reviews, 1 double bed, 1 bathroom
8–13 Jul
Top guest favourite
Room in Sharpsburg
Hidden Gem #1 - Stay with Dan and Alice.
4.97 out of 5 average rating, 178 reviews, 1 bed, 1 bathroom
8–13 Jul
Superhost
Home in Middletown
“The Rambler” In beautiful Middletown, MD ⛰
4.7 out of 5 average rating, 216 reviews, 4 bedrooms, 4 beds, 1.5 bathrooms
25–30 Jul
Top guest favourite
Home in Middletown
Spacious Frederick Cty Retreat
5.0 out of 5 average rating, 32 reviews, 3 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
Top guest favourite
Home in Frederick
Catoctin mountain getaway home
5.0 out of 5 average rating, 18 reviews, 4 bedrooms, 6 beds, 3.5 bathrooms
23–28 Jul
Top guest favourite
Home in Washington County
Trailhead House | Cozy Hiking Retreat
5.0 out of 5 average rating, 12 reviews, 5 bedrooms, 7 beds, 3 bathrooms
9–14 Oct
Top guest favourite
Flat in Boonsboro
46 South Main Suite #1
5.0 out of 5 average rating, 8 reviews, 1 bedroom, 2 beds, 1 bathroom
14–19 Oct
Top guest favourite
Home in Shepherdstown
WV Blue AND Gold (entire property)
5.0 out of 5 average rating, 14 reviews, 4 bedrooms, 9 beds, 2 bathrooms
2–7 Aug
Top guest favourite
Home in Middletown
Mountain Church Cottage
4.95 out of 5 average rating, 144 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
20–25 Jul
Home in Middletown
Secluded Farmhouse Retreat-Woods & Private Trails
3 bedrooms, 9 beds, 2 bathrooms
8–13 Jul
Superhost
Place to stay in Boonsboro
Firefly IV
5.0 out of 5 average rating, 3 reviews, 1 bedroom, 1 bed, 1 bathroom
8–13 Jul
Guest favourite
Home in Shepherdstown
Exclusive Wooded Chalet w Magnificent River Views
4.96 out of 5 average rating, 93 reviews, 4 bedrooms, 5 beds, 3.5 bathrooms
28 Aug – 2 Sept
Top guest favourite
Room in Middletown
Peaceful Farmette, Double Bedroom
4.97 out of 5 average rating, 197 reviews, 3 beds, 1 bathroom
12–17 Jul