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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
3 bedrooms, 3 beds, 2 bathrooms
17–22 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Boonsboro
The Overlook~ Exquisite Views
3 bedrooms, 4 beds, 2.5 bathrooms
19–24 Jul
4.91 out of 5 average rating, 47 reviews
Top guest favourite
Chalet in Boonsboro
Mountain Myst
3 bedrooms, 4 beds, 2.5 bathrooms
31 Aug – 5 Sept
4.94 out of 5 average rating, 612 reviews
Top guest favourite
Flat in Myersville
Hillside Hideaway
1 bedroom, 4 beds, 1 bathroom
12–17 Jul
4.94 out of 5 average rating, 31 reviews
Guest favourite
Room in Boonsboro
Dandelion
1 double bed, 1 bathroom
7–12 Jul
5.0 out of 5 average rating, 8 reviews
Room in Keedysville
Historic Civil War era stone house
2 beds, 1.5 bathrooms
7–12 Jul
4.81 out of 5 average rating, 293 reviews
Top guest favourite
Room in Sharpsburg
Hidden Gem #1 - Stay with Dan and Alice.
1 bed, 1 bathroom
8–13 Jul
4.97 out of 5 average rating, 178 reviews
Top guest favourite
Home in Middletown
Spacious Frederick Cty Retreat
3 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Home in Washington County
Trailhead House | Cozy Hiking Retreat
5 bedrooms, 7 beds, 3 bathrooms
9–14 Oct
5.0 out of 5 average rating, 12 reviews
Superhost
Home in Middletown
“The Rambler” In beautiful Middletown, MD ⛰
4 bedrooms, 4 beds, 1.5 bathrooms
25–30 Jul
4.7 out of 5 average rating, 216 reviews
Top guest favourite
Home in Frederick
Catoctin mountain getaway home
4 bedrooms, 6 beds, 3.5 bathrooms
23–28 Jul
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Flat in Boonsboro
46 South Main Suite #1
1 bedroom, 2 beds, 1 bathroom
14–19 Oct
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Shepherdstown
Exclusive Wooded Chalet w Magnificent River Views
4 bedrooms, 5 beds, 3.5 bathrooms
28 Aug – 2 Sept
4.96 out of 5 average rating, 93 reviews
Top guest favourite
Home in Middletown
Mountain Church Cottage
3 bedrooms, 3 beds, 2.5 bathrooms
20–25 Jul
4.95 out of 5 average rating, 144 reviews
Top guest favourite
Home in Shepherdstown
WV Blue AND Gold (entire property)
4 bedrooms, 9 beds, 2 bathrooms
2–7 Aug
5.0 out of 5 average rating, 14 reviews
Superhost
Place to stay in Boonsboro
Firefly IV
1 bedroom, 1 double bed, 1 bathroom
7–12 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Sharpsburg
Steps to Winery and Battlefield – 1 Acre Retreat
3 bedrooms, 3 queen beds, 1 bathroom
17–22 Aug
4.96 out of 5 average rating, 234 reviews
Top guest favourite
Room in Middletown
Peaceful Farmette, Double Bedroom
3 beds, 1 bathroom
12–17 Jul
4.97 out of 5 average rating, 197 reviews