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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
27 Sept – 2 Oct
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4.91 out of 5 average rating, 330 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
Guest favourite
Guest house in Middletown
Indulge, Fresh Flowers, Frederick County Haven
2 bedrooms, 3 beds, 1 bathroom
14–19 Oct
4.93 out of 5 average rating, 334 reviews
Top guest favourite
Home in Middletown
Spacious Frederick Cty Retreat
3 bedrooms, 4 beds, 2 bathrooms
22–27 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
12–17 Oct
4.95 out of 5 average rating, 155 reviews
Home in Middletown
“The Rambler” In beautiful Middletown, MD ⛰
4 bedrooms, 4 beds, 1.5 bathrooms
25–30 Oct
4.7 out of 5 average rating, 224 reviews
Top guest favourite
Room in Middletown
Peaceful Farmette, Blue Bedroom
1 queen bed, 1 bathroom
27 Sept – 2 Oct
4.98 out of 5 average rating, 324 reviews
Home in Middletown
Downtown Middletown Lodge
2 bedrooms, 3 beds, 1 bathroom
5–10 Oct
4.67 out of 5 average rating, 3 reviews
Guest favourite
Place to stay in Middletown
Vintage Mobile Home and Storage Workshop
1 bedroom, 1 queen bed, 1 bathroom
15–20 Sept
4.87 out of 5 average rating, 69 reviews
Home in Middletown
Updated Farmhouse < 2 Mi to Historic Middletown!
3 bedrooms, 4 beds, 2.5 bathrooms
22–27 Sept
4.9 out of 5 average rating, 10 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
Top guest favourite
Farm stay in Middletown
The Milk House at Hereford Grove Farm
1 bedroom, 1 king bed, 1 bathroom
12–17 Oct
4.95 out of 5 average rating, 79 reviews
Top guest favourite
Farm stay in Middletown
Fox Haven Organic Farm's Spring House
5 bedrooms, 14 beds, 2.5 bathrooms
27 Sept – 2 Oct
4.91 out of 5 average rating, 369 reviews
Top guest favourite
Guest suite in Middletown
Cozy Farmhouse Guest Suite w/ Private Deck
1 bedroom, 3 beds, 1 bathroom
15–20 Oct
4.95 out of 5 average rating, 43 reviews
Cabin in Middletown
Serene Log House Nestled Among the Battlefields
1 bedroom, 3 beds, 1 bathroom
26 Sept – 1 Oct
4.73 out of 5 average rating, 205 reviews
Guest favourite
Farm stay in Middletown
Another Adventure Farm
2 bedrooms, 2 beds, 2 bathrooms
25–30 Jun
4.93 out of 5 average rating, 29 reviews
Top guest favourite
Farm stay in Middletown
The Farm House at Hereford Grove Farm
3 bedrooms, 4 beds, 1.5 bathrooms
23–28 Oct
5.0 out of 5 average rating, 61 reviews
Top guest favourite
Home in Frederick
More Luxury = Gym + Entertainment + Best Location
4 bedrooms, 6 beds, 2.5 bathrooms
3–8 Nov
4.94 out of 5 average rating, 215 reviews
Top guest favourite
Townhouse in Frederick
Positive vibes on Market St
3 bedrooms, 3 beds, 1 bathroom
2–7 Nov
4.98 out of 5 average rating, 177 reviews