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Search results; 261 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, 38 reviews
Top guest favourite
Guest house in High Hill
Farm Stay+Eclectic Vintage+Fresh Eggs+EV Charge
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 58 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, 16 reviews
Guest favourite
Home in Montgomery City
2 Bed 1 Bath Montgomery City modern rail town stay
2 bedrooms, 2 beds, 1 bathroom
28 Sept – 3 Oct
4.89 out of 5 average rating, 9 reviews
Top guest favourite
Home in Troy
Secluded Lake House on a 13 acre private lake
3 bedrooms, 6 beds, 1.5 bathrooms
19–24 Oct
5.0 out of 5 average rating, 23 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
2 bedrooms, 3 beds, 1 bathroom
15–20 Sept
4.96 out of 5 average rating, 45 reviews
Guest favourite
Home in Troy
The Frontier House
2 bedrooms, 1 bed, 1 bathroom
11–16 Sept
5.0 out of 5 average rating, 9 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, 59 reviews
Top guest favourite
Apartment in Bowling Green
Cozy Townhouse Retreat
3 bedrooms, 4 beds, 2.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 70 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
Superhost
Home in Hermann
Hermann Retreat on Massas Creek
4 bedrooms, 10 beds, 2 bathrooms
13–18 Sept
4.86 out of 5 average rating, 21 reviews
Guest favourite
Home in Wright City
Serenity Shores by Innsbrook Vacations!
5 bedrooms, 16 beds, 5 bathrooms
27 Sept – 2 Oct
4.94 out of 5 average rating, 36 reviews
Top guest favourite
Home in Perry
Great location. Pet friendly.
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
4.89 out of 5 average rating, 28 reviews
Guest favourite
Home in Innsbrook
Aspen View by Innsbrook Vacations!
6 bedrooms, 12 beds, 5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 22 reviews
Guest favourite
Home in Hermann
Loutre Valley Farm Guest House
3 bedrooms, 4 beds, 2 bathrooms
2–7 Nov
4.95 out of 5 average rating, 19 reviews
Home in Hermann
The Woodland Retreat / Minutes from Hermann (A)
1 bedroom, 2 beds, 1 bathroom
11–16 Sept
New place to stay
Top guest favourite
Flat in Mexico
Promenade House - Apt D
1 bedroom, 2 queen beds, 1 bathroom
12–17 Sept
5.0 out of 5 average rating, 43 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