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Search results; 221 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
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4.97 out of 5 average rating, 38 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
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
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 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
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
Spacious country getaway
7 bedrooms, 7 beds, 3.5 bathrooms
1–8 Dec
5.0 out of 5 average rating, 16 reviews
Earthen home in Bellflower
Murray Acres Retreat | Earth Home on 20 Acres
2 bedrooms, 2 beds, 1 bathroom
5–10 Jan
Guest favourite
Cabin in Montgomery City
Secluded Getaway - Cozy Cabin Living
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Oct
4.91 out of 5 average rating, 47 reviews
Guest favourite
Home in Wright City
Country home L Level, private, kitchen, hot tub
1 bedroom, 2 queen beds, 1 bathroom
11–16 Sept
4.84 out of 5 average rating, 114 reviews
Flat in Jonesburg
1,711 Sq Ft Townhouse- 3Bed, 2.5 Bath
3 bedrooms, 3 beds, 2.5 bathrooms
19–26 Dec
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 Kingdom City
Retreat on the Creek
3 bedrooms, 7 beds, 1.5 bathrooms
13–18 Sept
4.88 out of 5 average rating, 60 reviews
Guest favourite
Flat in Troy
'Foxes Den' w/ Hot Tub, Pool Table & Fire Pit!
2 bedrooms, 3 beds, 1 bathroom
18–23 Oct
5.0 out of 5 average rating, 39 reviews
Top guest favourite
Bungalow in Troy
Welcome to the "Blue House on Boone"
2 bedrooms, 2 beds, 2 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 108 reviews
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
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
Guest favourite
Home in Bowling Green
Cozy blue home
2 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.9 out of 5 average rating, 51 reviews
Superhost
Home in Warrenton
Charming 1930s 2BR | Quiet Street | Warrenton MO
2 bedrooms, 3 beds, 1 bathroom
4–9 Oct
4.85 out of 5 average rating, 88 reviews