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Search results; 279 homes in Middletown

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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
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4.97 out of 5 average rating, 37 reviews
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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, 55 reviews
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Guest favourite
Home in Montgomery City
2 Bed 1 Bath Montgomery City modern rail town stay
2 bedrooms, 2 beds, 1 bathroom
1–6 Sept
4.89 out of 5 average rating, 9 reviews
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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
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Superhost
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
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Superhost
Home in Louisiana
The Yellow Rose Historic Home
4 bedrooms, 10 beds, 2 bathrooms
1–6 Sept
4.93 out of 5 average rating, 54 reviews
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Top guest favourite
Apartment in Bowling Green
Cozy Townhouse Retreat
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 69 reviews
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Top guest favourite
Home in Troy
Secluded Lake House on a 13 acre private lake
3 bedrooms, 6 beds, 1.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 23 reviews
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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
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Home in Mexico
NEW! Historical Schoolhouse experience 2026
1 bedroom, 2 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 4 reviews
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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
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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
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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
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Home in New Florence
John and Jan's Guesthouse clean & peaceful
2 bedrooms, 2 double beds, 1 bathroom
1–6 Sept
4.87 out of 5 average rating, 15 reviews
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Guest favourite
Flat in Montgomery City
2nd Street Stay
2 bedrooms, 4 beds, 1 bathroom
14–19 Sept
4.95 out of 5 average rating, 44 reviews
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Superhost
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
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Top guest favourite
Home in Bowling Green
Home away from Home
2 bedrooms, 4 beds, 1.5 bathrooms
1–6 Sept
4.95 out of 5 average rating, 199 reviews
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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
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Earthen home in Bellflower
Murray Acres Retreat | Earth Home on 20 Acres
2 bedrooms, 2 beds, 1 bathroom
5–10 Jan