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Search results; Over 1,000 homes in Middletown

Top 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
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
Guest favourite
Guest house in Middletown
Indulge, Fresh Flowers, Frederick County Haven
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
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
14–19 Sept
5.0 out of 5 average rating, 34 reviews
Top guest favourite
Farm stay in Middletown
The Milk House at Hereford Grove Farm
1 bedroom, 1 king bed, 1 bathroom
9–14 Sept
4.95 out of 5 average rating, 78 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
Home in Middletown
“The Rambler” In beautiful Middletown, MD ⛰
4 bedrooms, 4 beds, 1.5 bathrooms
11–16 Sept
4.7 out of 5 average rating, 224 reviews
Top guest favourite
Home in Middletown
Mountain Church Cottage
3 bedrooms, 3 beds, 2.5 bathrooms
9–14 Sept
4.95 out of 5 average rating, 155 reviews
Top guest favourite
Guest suite in Middletown
Cozy Farmhouse Guest Suite w/ Private Deck
1 bedroom, 3 beds, 1 bathroom
5–10 Oct
4.98 out of 5 average rating, 42 reviews
Guest favourite
Place to stay in Middletown
Vintage Mobile Home and Storage Workshop
1 bedroom, 1 queen bed, 1 bathroom
8–13 Sept
4.87 out of 5 average rating, 69 reviews
Home in Middletown
Downtown Middletown Lodge
2 bedrooms, 3 beds, 1 bathroom
12–17 Sept
4.67 out of 5 average rating, 3 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
Home in Jefferson
Firefly Hill Farmhouse
4 bedrooms, 4 beds, 2.5 bathrooms
9–14 Sept
4.95 out of 5 average rating, 61 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
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
Superhost
Place to stay in Frederick
Guest House near downtown Frederick
2 beds, 1 bathroom
9–14 Sept
4.88 out of 5 average rating, 49 reviews
Top guest favourite
Farm stay in Middletown
The Farm House at Hereford Grove Farm
3 bedrooms, 4 beds, 1.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 61 reviews
Top guest favourite
Guest house in Frederick
Boutique space at Marble Ridge
3 bedrooms, 3 queen beds, 1 bathroom
1–6 Nov
4.96 out of 5 average rating, 48 reviews
Home in Middletown
Updated Farmhouse < 2 Mi to Historic Middletown!
3 bedrooms, 4 beds, 2.5 bathrooms
29 Sept – 4 Oct
4.9 out of 5 average rating, 10 reviews