Middletown Vacation Rentals

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Vacation Rentals in Middletown

Owl house was built for unplugging, relaxing & connecting with friends/family

9.4 out of 10, Exceptional, (30)
"Great place to get away from it all. Clean, modern getaway in the woods with a great Jacuzzi."
$188 nightly
The price is $200
Aug 13 - Aug 14
Total includes taxes and fees
Owl house was built for unplugging, relaxing & connecting with friends/family

Cottage Properties - Country Log Cabin

10.0 out of 10, Exceptional, (164)
"Had a great time! "
Cottage Properties - Country Log Cabin

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.

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.

Cozy custom-built Cabin - Lakeside

10.0 out of 10, Exceptional, (54)
"Super cute little cabin with a great atmosphere, cute and homey feel with an amazing view"
Cozy custom-built Cabin - Lakeside

New custom-built TREEHOUSE - Sunrise

2.0 star property
10.0 out of 10, Exceptional, (11)
"5 star stay!"
New custom-built TREEHOUSE - Sunrise

Private Cabin on 90 Acres!

10.0 out of 10, Exceptional, (6)
Private Cabin on 90 Acres!

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.

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. "
$408 nightly
The price is $428
Aug 12 - Aug 13
Total includes taxes and fees
Sweet Retreat at Mark Twain Lake! Historic 4BR/2BA Dog & Family Friendly Home!

70's Park Side Cabin with Kayaks

9.8 out of 10, Exceptional, (35)
"The house was nice and convenient for spending time with family."
70's Park Side Cabin with Kayaks

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"

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

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

Seclusion at its finest on 90+ Acres

10.0 out of 10, Exceptional, (3)
"Quiet and lovely, excellent for any one who needs a quiet place to think and rest"
Seclusion at its finest on 90+ Acres

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
Aug 13 - Aug 14
Total includes taxes and fees
The Yellow Rose Historic Home

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 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

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.

The Venue at Hermann

10.0 out of 10, Exceptional, (3)
"Our stay at the property near Big Sping, MO was excellent. The venue was convenient for us to visit friends near the area. The room was as we expected, clean, bright and convenient. "
The Venue at Hermann

'Foxes Den' w/ Hot Tub, Pool Table & Fire Pit!

10.0 out of 10, Exceptional, (6)
"Lovely facility, well thought out. Everything we needed."
'Foxes Den' w/ Hot Tub, Pool Table & Fire Pit!
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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Frequently asked questions

Can I find a vacation rental in Middletown?

Yes, we give you a choice of vacation rentals near the most popular sights in Middletown, or you can select a secluded option if you're looking for relaxation.

What are some of the best vacation rentals in Middletown?

Hot Tub and Private Pool, 7 Bedroom, 4 Bathroom Home. Sleeps 16 comfortably.: This vacation home rental near Middletown offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a hot tub.

What’s there to see and do in Middletown?

While exploring the area, visit the sights like New Florence United Methodist Church, Stone Hill Winery, and Graham Cave State Park. In the larger area, you’ll also find Curling Vine Winery.

What’s a vacation rental in Middletown like?

Vacation rentals are private properties where you can stay for several days or longer in Middletown. Vacation rentals feature amenities such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from public hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a small group gathering.