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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
22–27 Aug
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4.9 out of 5 average rating, 323 reviews
Top guest favourite
Room in Middletown
Peaceful Farmette, Blue Bedroom
1 queen bed, 1 bathroom
16–21 Aug
4.98 out of 5 average rating, 321 reviews
Top guest favourite
Guest suite in Middletown
Cozy Farmhouse Guest Suite w/ Private Deck
1 bedroom, 3 beds, 1 bathroom
22–27 Aug
4.97 out of 5 average rating, 38 reviews
Guest favourite
Guest house in Middletown
Indulge, Fresh Flowers, Frederick County Haven
2 bedrooms, 3 beds, 1 bathroom
21–26 Aug
4.93 out of 5 average rating, 333 reviews
Top guest favourite
Home in Middletown
Spacious Frederick Cty Retreat
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 34 reviews
Top guest favourite
Home in Middletown
Mountain Church Cottage
3 bedrooms, 3 beds, 2.5 bathrooms
23–28 Aug
4.95 out of 5 average rating, 151 reviews
Guest favourite
Place to stay in Middletown
Vintage Mobile Home and Storage Workshop
1 bedroom, 1 queen bed, 1 bathroom
4–9 Sept
4.87 out of 5 average rating, 68 reviews
Home in Middletown
Downtown Middletown Lodge
2 bedrooms, 3 beds, 1 bathroom
10–15 Aug
New place to stay
Top guest favourite
Farm stay in Middletown
The Milk House at Hereford Grove Farm
1 bedroom, 1 king bed, 1 bathroom
24–29 Aug
4.95 out of 5 average rating, 75 reviews
Home in Middletown
“The Rambler” In beautiful Middletown, MD ⛰
4 bedrooms, 4 beds, 1.5 bathrooms
6–11 Sept
4.69 out of 5 average rating, 221 reviews
Top guest favourite
Home in Middletown
Beautiful historical town, 3 bedrooms, countryside
3 bedrooms, 3 beds, 3 bathrooms
9–14 Nov
4.97 out of 5 average rating, 91 reviews
Top guest favourite
Farm stay in Middletown
Fox Haven Organic Farm's Spring House
5 bedrooms, 14 beds, 2.5 bathrooms
16–21 Aug
4.91 out of 5 average rating, 365 reviews
Home in Middletown
Updated Farmhouse < 2 Mi to Historic Middletown!
3 bedrooms, 4 beds, 2.5 bathrooms
6–11 Sept
4.9 out of 5 average rating, 10 reviews
Top guest favourite
Farm stay in Middletown
Getaway on the Catoctin
1 bedroom, 3 beds, 1 bathroom
11–16 Aug
5.0 out of 5 average rating, 40 reviews
Top guest favourite
Farm stay in Middletown
The Farm House at Hereford Grove Farm
3 bedrooms, 4 beds, 1.5 bathrooms
11–16 Aug
5.0 out of 5 average rating, 60 reviews
Superhost
Flat in Middletown
Woodsy Lair in Historic Middletown Valley!
2 beds, 1 bathroom
23–28 Aug
4.66 out of 5 average rating, 62 reviews
Guest favourite
Cabin in Middletown
Charming vintage cabin in the ❤️ of Middletown.
1 bedroom, 1 queen bed, 1 bathroom
24–29 Oct
4.9 out of 5 average rating, 466 reviews
Guest favourite
Place to stay in Frederick
Tiny A-Frame Retreat in the Woods
1 bedroom, 1 bed, 1 bathroom
28 Aug – 2 Sept
4.9 out of 5 average rating, 154 reviews
Top guest favourite
Treehouse in Smithsburg
Bin There Treehouse, a grain bin treehouse!
1 bedroom, 2 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 25 reviews