Middletown Vacation Rentals
Get more for your budget and save up to 50% off select Secret Bargain hotels
Get even more value with CheapTickets Price Guarantee!
Change your flight without a fee on select flights
Vacation Rentals in Middletown
Hot Tub and Private Pool, 7 Bedroom, 4 Bathroom Home. Sleeps 16 comfortably.
Warrenton MO
With a stay at this vacation home in Warrenton, you'll be within a 10-minute walk of Veterans Memorial Park and Khory Park.
Secluded 2 bedroom home close to Hermann
New Florence MO
$237 nightly
The price is $250 total per night
$250 total
Dec 8 - Dec 9
Total with taxes and fees
Located in New Florence, this vacation home is in a rural location, within a 15-minute drive of Endless Summer Winery and Katy Trail - McKittrick Trailhead.
Historic Main Street Cottage
Troy MO
With a stay at this vacation home in Troy, you'll be within a 5-minute walk of Glenna's Garden and Troy Missouri Main Street Park.
The Chicken Coop on Highway H
Troy MO
Located in Troy, this vacation home is in a rural location, within a 15-minute walk of Glenna's Garden and Troy Missouri Main Street Park.
A real charmer built in 1915 , pet friendly , located next to Mark Twain lake.
Perry MO
A stay at this vacation home places you in the heart of Perry, just a 3-minute walk from Bill Trower Memorial Park and within a 5-minute drive of Perry Park.
Kitchen
Washer
The Yellow Rose Historic Home
Louisiana MO
$333 nightly
The price is $343 total per night
$343 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
Located in Louisiana, this vacation home is a 1-minute drive from Mississippi River and 9 minutes from Clarksville State Game Refuge.
Kitchen
Washer
Sweet Cherry Escape | JZ Vacation Rentals
516 Cherry Lane Warrenton MO
With a stay at this vacation home in Warrenton, you'll be a 3-minute walk from Dyer Park and 11 minutes by foot from Khory Park.
4K Ranch - 10 acre property & home near Hermann
New Florence MO
Located in New Florence, this vacation home is in a rural location, within a 15-minute drive of Endless Summer Winery and Curling Vine Winery.
Kitchen
Washer
Relaxing, Quiet get away where you can enjoy the outdoors.
Elsberry MO
This family-friendly vacation home is 6.7 mi (10.8 km) from Cuivre River State Park and 7.5 mi (12.1 km) from Lincoln Hills Natural Area.
Kitchen
Washer
Welcome to the "Blue House on Boone"
Troy MO
With a stay at this vacation home in Troy, you'll be just steps from Glenna's Garden and Troy Missouri Main Street Park.
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.
Middletown Vacation Rentals essential information
Accommodation | 12 Vacation Rentals |
|---|---|
Lowest Price | $250 |
Highest Price | $343 |
Popular accommodation | Hot Tub and Private Pool, 7 Bedroom, 4 Bathroom Home. Sleeps 16 comfortably., Secluded 2 bedroom home close to Hermann, Historic Main Street Cottage, The Chicken Coop on Highway H, A real charmer built in 1915 , pet friendly , located next to Mark Twain lake., The Yellow Rose Historic Home, Sweet Cherry Escape | JZ Vacation Rentals, 4K Ranch - 10 acre property & home near Hermann, Relaxing, Quiet get away where you can enjoy the outdoors., Welcome to the "Blue House on Boone", DairyLand - A Private Getaway on 16 acres next door to Dairy Farm with EV Hookup, Sweet Cherry Escape | JZ Vacation Rentals |