Middletown Vacation Rentals

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Middletown Vacation Homes

Historic Main Street Cottage
Stroll through the serene garden, surrounded by a variety of flowering plants and shrubs, under the shade of a large tree.

Historic Main Street Cottage

10.0 out of 10, Exceptional, (30)
"The house was great! There was plenty of space for all of us, and we can't wait to come back!"
Historic Main Street Cottage
Hot Tub and Private Pool, 7 Bedroom, 4 Bathroom Home. Sleeps 16 comfortably.
Relax by the serene pool surrounded by lush greenery and a charming wooden bench.

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

8.8 out of 10, Excellent, (18)
"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.
A real charmer built in 1915 , pet friendly , located next to Mark Twain lake.
Enjoy a room with a sloped ceiling, skylight, and wooden staircase.

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

10.0 out of 10, Exceptional, (20)
"We enjoyed every minute in this charming home It was very clean and came with everything we needed I will be back Chris was very helpful and quick to respond to all my questions "
A real charmer built in 1915 , pet friendly , located next to Mark Twain lake.
STORMFIELD WEST Country charm nestled in Perry Mo, 3 miles from Mark Twain Lake
Enjoy meals in this stylish dining area with a round table and six comfortable chairs.

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

9.4 out of 10, Exceptional, (6)
"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
Welcome to the "Blue House on Boone"
Enjoy cooking in this well-lit kitchen with an oven, microwave, and sink.

Welcome to the "Blue House on Boone"

10.0 out of 10, Exceptional, (36)
"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"
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, (1)
"Responses from the owners were swift, the home was beautiful, the morning cows made the morning much brighter, all the necessities needed for the stay inside the home were there. The bedding was nice and comfy, the coffee bar and board game options were lovely. 10/10 would recommend this location. "
DairyLand - A Private Getaway on 16 acres next door to Dairy Farm with EV Hookup
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. "
The price is CA $356
CA $592 total
includes taxes & fees
Aug 11 - Aug 12
Sweet Retreat at Mark Twain Lake! Historic 4BR/2BA Dog & Family Friendly Home!
The Yellow Rose Historic Home
Classic bedroom with a four-poster bed, dresser, and large mirror.

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"
The price is CA $303
CA $432 total
includes taxes & fees
Aug 13 - Aug 14
The Yellow Rose Historic Home
The Chicken Coop on Highway H
Enjoy cooking in this well-equipped kitchen with a coffee machine, refrigerator, and microwave.

The Chicken Coop on Highway H

10.0 out of 10, Exceptional, (13)
"We enjoyed our stay at the Chicken Coop! Nice home, very clean and good location for Troy. "
The Chicken Coop on Highway H
4K Ranch - 10 acre property & home near Hermann
Relax in this stylish living area with a large sofa, dining table, and kitchen in the background.

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
Relaxing, Quiet get away where you can enjoy the outdoors.
Relax in a serene bedroom with a large bed, dark grey headboard, and wooden panel design.

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

10.0 out of 10, Exceptional, (27)
"This a second time we have stayed at this property. It is perfect for our family."
Relaxing, Quiet get away where you can enjoy the outdoors.
Sweet Cherry Escape | JZ Vacation Rentals
Enjoy a shaded outdoor space with a wooden deck and staircase, surrounded by a grassy yard and a large tree.

Sweet Cherry Escape | JZ Vacation Rentals

3.0 star property
Sweet Cherry Escape | JZ Vacation Rentals
Sweet Cherry Escape | JZ Vacation Rentals
Enjoy a serene outdoor space with a covered area, bench, and wooden deck.

Sweet Cherry Escape | JZ Vacation Rentals

9.4 out of 10, Exceptional, (31)
"Cute 2 bedroom home, was perfect for our weekend to visit the family "
Sweet Cherry Escape | JZ Vacation Rentals
Secluded 2 bedroom home close to Hermann
Relax on the covered patio surrounded by lush greenery and enjoy the fire pit.

Secluded 2 bedroom home close to Hermann

9.8 out of 10, Exceptional, (38)
"We only had a short stay, but it was very nice. Such a cute, secluded place right outside of Herman. Worked out perfect for our winery tour. "
The price is CA $248
CA $345 total
includes taxes & fees
Aug 21 - Aug 22
Secluded 2 bedroom home close to Hermann
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

Private Cabin on 90 Acres!

Private Cabin on 90 Acres!

10/10 Excellent
"Peaceful and relaxing stay. Beautiful inside, welll designed and the bed was VERY comfortable! Hot tub was an absolute plus!! The only recommendation I would have was to have a sand entryway to the pond so you can float around and easy access for the kayaks. We will will be back!! "
Melissa T. 4-night trip
Posted 2 days ago
Private Cabin on 90 Acres!