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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
Room in Sharpsburg
Hidden Gem #1 - Stay with Dan and Alice.
1 bed, 1 bathroom
21–26 Jul
4.97 out of 5 average rating, 178 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
Flat in Myersville
Hillside Hideaway
1 bedroom, 4 beds, 1 bathroom
12–17 Jul
4.94 out of 5 average rating, 31 reviews
Room in Keedysville
Historic Civil War era stone house
2 beds, 1.5 bathrooms
8–13 Jul
4.81 out of 5 average rating, 293 reviews
Top guest favourite
Guest suite in Middletown
Cozy Farmhouse Guest Suite w/ Private Deck
1 bedroom, 3 beds, 1 bathroom
4–9 Aug
4.97 out of 5 average rating, 35 reviews
Place to stay in Hagerstown
Peaceful and serene comfy room in family home!
1 bedroom, 1 queen bed, 2 bathrooms
16–21 Jul
New place to stay
Top guest favourite
Room in Middletown
Peaceful Farmette, Blue Bedroom
1 queen bed, 1 bathroom
12–17 Jul
4.98 out of 5 average rating, 316 reviews
Top guest favourite
Cabin in Myersville
Spruce Run Cabin, a wooded retreat on the mountain
2 bedrooms, 2 beds, 2 bathrooms
26 Sept – 1 Oct
4.96 out of 5 average rating, 102 reviews
Top guest favourite
Guest house in Smithsburg
Jewel Vinsota Artist's Guesthouse
1 bedroom, 1 double bed, 1 bathroom
31 Aug – 5 Sept
4.97 out of 5 average rating, 845 reviews
Superhost
Cabin in Keedysville
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
3 bedrooms, 4 beds, 3 bathrooms
9–14 Aug
4.9 out of 5 average rating, 162 reviews
Top guest favourite
Flat in Hagerstown
Private, relaxing, scenic 2 bdrm unit, Sleeps 1-5
2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
4.99 out of 5 average rating, 169 reviews
Home in Middletown
Secluded Farmhouse Retreat-Woods & Private Trails
3 bedrooms, 9 beds, 2 bathrooms
8–13 Jul
Top guest favourite
Home in Middletown
Beautiful historical town, 3 bedrooms, countryside
3 bedrooms, 3 beds, 3 bathrooms
27 Oct – 1 Nov
4.97 out of 5 average rating, 90 reviews
Guest favourite
Guest suite in Myersville
Harmony Lodge nestled in wooded tranquility!
2 bedrooms, 2 queen beds, 1 bathroom
30 Aug – 4 Sept
4.91 out of 5 average rating, 339 reviews
Top guest favourite
Cottage in Hagerstown
Unique historic home - Springhouse 1803
3 bedrooms, 4 beds, 1 bathroom
26–31 Jul
4.96 out of 5 average rating, 461 reviews
Guest favourite
Room in Boonsboro
Dandelion
1 double bed, 1 bathroom
8–13 Jul
5.0 out of 5 average rating, 8 reviews
Guest favourite
Cottage in Middletown
Charming "Cream of the Crop" Cape ~❤️of Middletown
2 bedrooms, 2 beds, 2.5 bathrooms
26–31 Jul
4.9 out of 5 average rating, 320 reviews