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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
10–15 Aug
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4.94 out of 5 average rating, 613 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
Flat in Myersville
Hillside Hideaway
4.94 out of 5 average rating, 31 reviews, 1 bedroom, 4 beds, 1 bathroom
21–26 Jul
Superhost
Home in Myersville
Hillside Haven
New place to stay, 3 bedrooms, 5 beds, 1.5 bathrooms
20–25 Jul
Top guest favourite
Home in Boonsboro
The Overlook~ Exquisite Views
4.92 out of 5 average rating, 48 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
14–19 Aug
Top guest favourite
Home in Myersville
The Crooked Cottage: a Cozy, Curated Escape
4.98 out of 5 average rating, 310 reviews, 2 bedrooms, 2 beds, 2 bathrooms
15–20 Aug
Top guest favourite
Cabin in Boonsboro
Little Lodge
4.95 out of 5 average rating, 443 reviews, 2 bedrooms, 3 beds, 1 bathroom
14–19 Aug
Top guest favourite
Room in Sharpsburg
Hidden Gem #1 - Stay with Dan and Alice.
4.97 out of 5 average rating, 182 reviews, 1 bed, 1 bathroom
2–7 Aug
Home in Keedysville
Bufflehead Lodge
New place to stay, 2 bedrooms, 3 beds, 2 bathrooms
27 Jul – 1 Aug
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
Room in Keedysville
Historic Civil War era stone house
4.81 out of 5 average rating, 293 reviews, 2 beds, 1.5 bathrooms
20–25 Jul
Top guest favourite
Cottage in Hagerstown
Unique historic home - Springhouse 1803
4.96 out of 5 average rating, 463 reviews, 3 bedrooms, 4 beds, 1 bathroom
16–21 Aug
Cabin in Hedgesville
A-frame Retreat, HotTub, Arcade, Golf, Dogs OK
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
13–18 Sept
Guest favourite
Cottage in Middletown
Charming "Cream of the Crop" Cape ~❤️of Middletown
4.9 out of 5 average rating, 321 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
12–17 Aug
Guest favourite
Tiny home in Jefferson County
❤️ Secluded 1940s Romantic Tiny House on the River
4.88 out of 5 average rating, 519 reviews, 1 bed, WC
23–28 Aug
Home in Hagerstown
5br 2.5ba Comfy house near Meritus Medical Complex
5 bedrooms, 5 beds, 2.5 bathrooms
26–31 Jul
Top guest favourite
Home in Martinsburg
1900 Newton School-house
4.98 out of 5 average rating, 43 reviews, 1 bed, 1 bathroom
25–30 Aug
Guest favourite
Room in Boonsboro
Dandelion
5.0 out of 5 average rating, 8 reviews, 1 double bed, 1 bathroom
29 Jul – 3 Aug
Top guest favourite
Guest suite in Middletown
Cozy Farmhouse Guest Suite w/ Private Deck
4.97 out of 5 average rating, 36 reviews, 1 bedroom, 3 beds, 1 bathroom
4–9 Aug