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Search results; 272 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+Eclectic Vintage+EV Charge
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 57 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
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 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
Apartment in Bowling Green
Cozy Townhouse Retreat
3 bedrooms, 4 beds, 2.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 69 reviews
Guest favourite
Home in Montgomery City
2 Bed 1 Bath Montgomery City modern rail town stay
2 bedrooms, 2 beds, 1 bathroom
11–16 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
Home in Perry
Great location. Pet friendly.
3 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
4.93 out of 5 average rating, 27 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
Top guest favourite
Home in Wright City
Eagle Estate-A private gated property
7 bedrooms, 9 beds, 7.5 bathrooms
9–14 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
Top guest favourite
Home in Troy
The Frontier House
2 bedrooms, 1 bed, 1 bathroom
9–14 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in New Florence
Spacious Five Bedroom Country Home near Hermann MO
5 bedrooms, 5 beds, 3 bathrooms
4–9 Oct
4.93 out of 5 average rating, 45 reviews
Guest favourite
Home in Hermann
Loutre Valley Farm Guest House
3 bedrooms, 4 beds, 2 bathrooms
27 Oct – 1 Nov
4.95 out of 5 average rating, 19 reviews
Home in Mexico
NEW! Historical Schoolhouse experience 2026
1 bedroom, 2 beds, 1 bathroom
19–24 Sept
5.0 out of 5 average rating, 4 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
Top guest favourite
Home in Jonesburg
Quiet Country 3 Bedroom Escape
3 bedrooms, 7 beds, 3 bathrooms
11–16 Sept
5.0 out of 5 average rating, 31 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