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Search results; Over 1,000 homes in Middletown

Guest favourite
Cottage in Middletown
Charming "Cream of the Crop" Cape ~❤️of Middletown
2 bedrooms, 2 beds, 2.5 private bathrooms
2–7 Aug
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4.9 out of 5 average rating, 321 reviews
Top guest favourite
Room in Middletown
Peaceful Farmette, Red Bedroom
4.98 out of 5 average rating, 218 reviews, 1 double bed, 1 bathroom
16–21 Jul
Top guest favourite
Home in Middletown
Mountain Church Cottage
4.95 out of 5 average rating, 146 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
20–25 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
Guest favourite
Guest house in Middletown
Indulge, Fresh Flowers, Frederick County Haven
4.93 out of 5 average rating, 329 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 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
Home in Middletown
“The Rambler” In beautiful Middletown, MD ⛰
4.7 out of 5 average rating, 217 reviews, 4 bedrooms, 4 beds, 1.5 bathrooms
25–30 Jul
Top guest favourite
Home in Middletown
Beautiful historical town, 3 bedrooms, countryside
4.97 out of 5 average rating, 91 reviews, 3 bedrooms, 3 beds, 3 bathrooms
8–13 Nov
Top guest favourite
Farm stay in Middletown
The Milk House at Hereford Grove Farm
4.96 out of 5 average rating, 71 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Jul
Guest favourite
Place to stay in Middletown
Vintage Mobile Home and Storage Workshop
4.87 out of 5 average rating, 67 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Jul
Home in Middletown
Updated Farmhouse < 2 Mi to Historic Middletown!
4.88 out of 5 average rating, 8 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
6–11 Sept
Top guest favourite
Farm stay in Middletown
Getaway on the Catoctin
5.0 out of 5 average rating, 38 reviews, 1 bedroom, 3 beds, 1 bathroom
24–29 Aug
Top guest favourite
Farm stay in Middletown
Fox Haven Organic Farm's Spring House
4.91 out of 5 average rating, 365 reviews, 5 bedrooms, 14 beds, 2.5 bathrooms
2–7 Aug
Superhost
Flat in Middletown
Woodsy Lair in Historic Middletown Valley!
4.66 out of 5 average rating, 62 reviews, 2 beds, 1 bathroom
20–25 Jul
Home in Smithsburg
The Farmhouse
New place to stay, 2 bedrooms, 3 beds, 1 bathroom
24–29 Jul
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 Myersville
Sleepy Hollow Log Cabin
4.96 out of 5 average rating, 208 reviews, 2 bedrooms, 4 beds, 1 bathroom
19–24 Jul
Guest house in Thurmont
Catoctin Cabin
New place to stay, 1 bedroom, 4 beds, 1 bathroom
20–25 Jul
Top guest favourite
Farm stay in Middletown
The Farm House at Hereford Grove Farm
5.0 out of 5 average rating, 60 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
24–29 Jul