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Search results; 278 homes in Middletown

Top guest favourite
Cabin in Middletown
Papa's Cabin - 40 acres & 5 acre lake!
2 bedrooms, 5 beds, 2 private bathrooms
27 Nov – 2 Dec
,
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
Guest favourite
Home in Montgomery City
Spacious country getaway
7 bedrooms, 7 beds, 3.5 bathrooms
1–8 Dec
5.0 out of 5 average rating, 14 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
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
Top guest favourite
Apartment in Bowling Green
Cozy Townhouse Retreat
3 bedrooms, 4 beds, 2.5 bathrooms
3–8 Sept
5.0 out of 5 average rating, 69 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
Home in Perry
Great location on Highway J in Perry!
3 bedrooms, 5 beds, 1 bathroom
10–15 Sept
5.0 out of 5 average rating, 5 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
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
Top guest favourite
Home in Wright City
Eagle Estate-A private gated property
7 bedrooms, 9 beds, 7.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 43 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
Guest favourite
Home in Mexico
The Lakeview Park Retreat • King Bed & Views
2 bedrooms, 2 queen beds, 1 bathroom
3–8 Sept
4.85 out of 5 average rating, 75 reviews
Home in New Florence
John and Jan's Guesthouse clean & peaceful
2 bedrooms, 2 double beds, 1 bathroom
3–8 Sept
4.87 out of 5 average rating, 15 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
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
Top guest favourite
Flat in Mexico
Promenade House - Apt D
1 bedroom, 2 queen beds, 1 bathroom
3–8 Sept
5.0 out of 5 average rating, 43 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