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Search results; Over 1,000 homes in Middletown

Guest favourite
Flat in Middletown
The Poplar Place at the foot of South Mountain!
2 bedrooms, 3 beds, 1.5 private bathrooms
26–31 Oct
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4.86 out of 5 average rating, 56 reviews
Guest favourite
Cottage in Middletown
Charming "Cream of the Crop" Cape ~❤️of Middletown
2 bedrooms, 2 beds, 2.5 bathrooms
2–7 Aug
4.9 out of 5 average rating, 322 reviews
Top guest favourite
Room in Middletown
Peaceful Farmette, Blue Bedroom
1 queen bed, 1 bathroom
1–6 Aug
4.98 out of 5 average rating, 319 reviews
Top guest favourite
Home in Middletown
Mountain Church Cottage
3 bedrooms, 3 beds, 2.5 bathrooms
9–14 Aug
4.95 out of 5 average rating, 148 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, 37 reviews
Guest favourite
Guest house in Middletown
Indulge, Fresh Flowers, Frederick County Haven
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
4.93 out of 5 average rating, 332 reviews
Home in Middletown
“The Rambler” In beautiful Middletown, MD ⛰
4 bedrooms, 4 beds, 1.5 bathrooms
10–15 Aug
4.7 out of 5 average rating, 220 reviews
Top guest favourite
Home in Middletown
Spacious Frederick Cty Retreat
3 bedrooms, 4 beds, 2 bathrooms
10–15 Aug
5.0 out of 5 average rating, 33 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
Top guest favourite
Home in Middletown
Beautiful historical town, 3 bedrooms, countryside
3 bedrooms, 3 beds, 3 bathrooms
2–7 Nov
4.97 out of 5 average rating, 91 reviews
Top guest favourite
Farm stay in Middletown
The Milk House at Hereford Grove Farm
1 bedroom, 1 king bed, 1 bathroom
1–6 Aug
4.95 out of 5 average rating, 74 reviews
Top guest favourite
Farm stay in Middletown
Getaway on the Catoctin
1 bedroom, 3 beds, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 39 reviews
Guest favourite
Home in Middletown
Updated Farmhouse < 2 Mi to Historic Middletown!
3 bedrooms, 4 beds, 2.5 bathrooms
6–11 Sept
4.89 out of 5 average rating, 9 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
Top guest favourite
Farm stay in Middletown
Fox Haven Organic Farm's Spring House
5 bedrooms, 14 beds, 2.5 bathrooms
2–7 Aug
4.91 out of 5 average rating, 365 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
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
Home in Middletown
Downtown Middletown Lodge
1 bedroom, 3 beds, 1 bathroom
1–6 Aug
New place to stay
Superhost
Farm stay in Woodsboro
Farm Retreat- Sauna, Hot Tub, Cold Plunge, Trails
4 bedrooms, 4 beds, 2 bathrooms
12–17 Aug
5.0 out of 5 average rating, 3 reviews