Search Vacation Homes in Middletown

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Oct 10 - Oct 12
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Dec 19 - Dec 21
In four months
Jan 16 - Jan 18

Vacation Homes in Middletown

Secluded 2 bedroom home close to Hermann
Outdoor dining

Secluded 2 bedroom home close to Hermann

9.8 out of 10, Exceptional, (40)
"We thoroughly enjoyed our stay! The house was very clean and spacious for our group of 6. Very happy with our experience!"
$237 nightly
The price is $250
Sep 29 - Sep 30
Total with taxes and fees
Secluded 2 bedroom home close to Hermann
Hot Tub and Private Pool, 7 Bedroom, 4 Bathroom Home. Sleeps 16 comfortably.
Outdoor pool

Hot Tub and Private Pool, 7 Bedroom, 4 Bathroom Home. Sleeps 16 comfortably.

8.8 out of 10, Excellent, (20)
"We had a great time at this location. It was cute, clean, and well maintained."
Hot Tub and Private Pool, 7 Bedroom, 4 Bathroom Home. Sleeps 16 comfortably.
DairyLand - A Private Getaway on 16 acres next door to Dairy Farm with EV Hookup
Terrace/patio

DairyLand - A Private Getaway on 16 acres next door to Dairy Farm with EV Hookup

10.0 out of 10, Exceptional, (2)
"Location is very quiet and home was awesome. "
DairyLand - A Private Getaway on 16 acres next door to Dairy Farm with EV Hookup
Welcome to the "Blue House on Boone"
Fridge, microwave, oven, stovetop

Welcome to the "Blue House on Boone"

10.0 out of 10, Exceptional, (38)
"Great place to stay. Very cozy and owners were quick to respond to any questions we had prior to our arrival and during our stay. Great communication and will book again if we are in the area traveling. "
Welcome to the "Blue House on Boone"
A real charmer built in 1915 , pet friendly , located next to Mark Twain lake.
Interior

A real charmer built in 1915 , pet friendly , located next to Mark Twain lake.

10.0 out of 10, Exceptional, (22)
"Cozy and comfortable stay during our church conference. The home was clean, well-equipped, and peaceful—just what we needed. Would definitely recommend and stay again!"
A real charmer built in 1915 , pet friendly , located next to Mark Twain lake.
Sweet Retreat at Mark Twain Lake! Historic 4BR/2BA Dog & Family Friendly Home!
Fridge, microwave, oven, stovetop

Sweet Retreat at Mark Twain Lake! Historic 4BR/2BA Dog & Family Friendly Home!

10.0 out of 10, Exceptional, (3)
"The house was great - just as advertised, safe, quiet. A real architectural gem. We had 7 and a puppy and it all worked out great. Loved the patio and fire pit. "
$410 nightly
The price is $430
Sep 29 - Sep 30
Total with taxes and fees
Sweet Retreat at Mark Twain Lake! Historic 4BR/2BA Dog & Family Friendly Home!
Sweet Cherry Escape | JZ Vacation Rentals
Exterior

Sweet Cherry Escape | JZ Vacation Rentals

3.0 star property
Sweet Cherry Escape | JZ Vacation Rentals
STORMFIELD WEST Country charm nestled in Perry Mo, 3 miles from Mark Twain Lake
Dining

STORMFIELD WEST Country charm nestled in Perry Mo, 3 miles from Mark Twain Lake

9.2 out of 10, Wonderful, (7)
"Check in was easy. plenty of room for the 10 of us. "
STORMFIELD WEST Country charm nestled in Perry Mo, 3 miles from Mark Twain Lake
Historic Main Street Cottage
Property grounds

Historic Main Street Cottage

10.0 out of 10, Exceptional, (34)
"Was in town for a funeral. Comfy cozy place will be staying again when i have to come back to Troy "
Historic Main Street Cottage
The Chicken Coop on Highway H
Fridge, microwave, oven, stovetop

The Chicken Coop on Highway H

10.0 out of 10, Exceptional, (15)
"Just an excellent place to stay, we were here for a family reunion and it was so great for family and friends to drop in. Lots of room and a bonus for kids with the ping pong and foosball table down stairs. The kitchen is well equipped, will stay here again "
The Chicken Coop on Highway H
4K Ranch - 10 acre property & home near Hermann
Smart TV, books

4K Ranch - 10 acre property & home near Hermann

10.0 out of 10, Exceptional, (12)
"We stayed here for a weekend getaway with friends. The property was perfect distance from Hermann and had tons of fun spaces! We can’t wait to stay here again!"
4K Ranch - 10 acre property & home near Hermann
The Yellow Rose Historic Home
5 bedrooms, desk, travel crib, free WiFi

The Yellow Rose Historic Home

10.0 out of 10, Exceptional, (11)
"We are 7 sisters aged 50-76. We had a wonderful stay at the Yellow Rose. This beautiful old home had rooms and beds for all of us. Would definitely stay here again"
$306 nightly
The price is $314
Sep 29 - Sep 30
Total with taxes and fees
The Yellow Rose Historic Home
Relaxing, Quiet get away where you can enjoy the outdoors.
4 bedrooms, free WiFi, bed sheets

Relaxing, Quiet get away where you can enjoy the outdoors.

10.0 out of 10, Exceptional, (28)
"The venue was quiet and peaceful."
Relaxing, Quiet get away where you can enjoy the outdoors.
Sweet Cherry Escape | JZ Vacation Rentals
Exterior

Sweet Cherry Escape | JZ Vacation Rentals

9.4 out of 10, Exceptional, (31)
"Very clean, comfortable beds, updates throughout for a home built in the 1930’s, and the hosts have excellent communication throughout your entire stay…..highly recommend!"
Sweet Cherry Escape | JZ Vacation Rentals
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Middletown Hotel Reviews

Super 8 by Wyndham Warrenton

Super 8 by Wyndham Warrenton

10/10 Excellent
"Nice to be able to use Hotel.com when we decide it is time to stop for the night"
Andrew 1-night trip
Posted 6 days ago
Super 8 by Wyndham Warrenton

Find out more about Middletown

Find out more about Middletown

Middletown Vacation Homes information

Number of reviews
255
Accommodation
14 Vacation Homes
Lowest Price
$250
Highest Price
$430

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