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Search results; 273 homes in Middletown

Top guest favourite
Cabin in Middletown
Papa's Cabin - 40 acres & 5 acre lake!
2 bedrooms, 5 beds, 2 private bathrooms
5–10 Sept
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4.97 out of 5 average rating, 37 reviews
Top guest favourite
Guest house in High Hill
Farm Stay+Fresh Eggs+Eclectic Vintage+EV Charge
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 56 reviews
Top guest favourite
Cottage in Montgomery City
Small private country home with lake, spa, firepit
1 bedroom, 1 queen bed, 1 bathroom
21–26 Sept
4.99 out of 5 average rating, 415 reviews
Guest favourite
Home in Montgomery City
2 Bed 1 Bath Montgomery City modern rail town stay
2 bedrooms, 2 beds, 1 bathroom
4–9 Sept
4.89 out of 5 average rating, 9 reviews
Top guest favourite
Apartment in Bowling Green
Cozy Townhouse Retreat
3 bedrooms, 4 beds, 2.5 bathrooms
2–7 Sept
5.0 out of 5 average rating, 69 reviews
Home in Hermann
Hermann Hideaway / Private Woodland Retreat (B)
1 bedroom, 1 king bed, 1 bathroom
2–7 Sept
New place to stay
Top guest favourite
Home in New Florence
4K Ranch - 10 acre property & home near Hermann
3 bedrooms, 8 beds, 1 bathroom
11–16 Oct
4.98 out of 5 average rating, 58 reviews
Guest favourite
Home in Vandalia
Cozy White Bungalow
2 bedrooms, 2 beds, 1 bathroom
16–21 Sept
4.79 out of 5 average rating, 34 reviews
Guest favourite
Flat in Montgomery City
2nd Street Stay - Upstairs Suite
2 bedrooms, 3 beds, 1 bathroom
1–6 Jan
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Home in Troy
The Frontier House
2 bedrooms, 1 bed, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 7 reviews
Superhost
Home in Hermann
Hermann Retreat on Massas Creek
4 bedrooms, 10 beds, 2 bathrooms
6–11 Sept
4.85 out of 5 average rating, 20 reviews
Guest favourite
Home in New Florence
Secluded 2 bedroom home close to Hermann
2 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
4.83 out of 5 average rating, 53 reviews
Home in New Florence
John and Jan's Guesthouse clean & peaceful
2 bedrooms, 2 double beds, 1 bathroom
2–7 Sept
4.87 out of 5 average rating, 15 reviews
Superhost
Home in Warrenton
The Hiding Place - Private Pool and Spa, sleeps 16
7 bedrooms, 9 beds, 4 bathrooms
27 Sept – 2 Oct
4.82 out of 5 average rating, 55 reviews
Guest favourite
Home in Mexico
The Lakeview Park Retreat • King Bed & Views
2 bedrooms, 2 queen beds, 1 bathroom
2–7 Sept
4.85 out of 5 average rating, 75 reviews
Top guest favourite
Home in Perry
Great location. Pet friendly.
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
4.92 out of 5 average rating, 26 reviews
Top guest favourite
Home in Bowling Green
Home away from Home
2 bedrooms, 4 beds, 1.5 bathrooms
13–18 Sept
4.95 out of 5 average rating, 199 reviews
Room in Louisiana
Relax, Unwind & Explore Louisiana, MO
1 bed, 3 bathrooms
2–7 Sept
New place to stay
Guest favourite
Home in Hermann
Loutre Valley Farm Guest House
3 bedrooms, 4 beds, 2 bathrooms
27 Oct – 1 Nov
4.94 out of 5 average rating, 18 reviews