Holiday Rentals in Middletown

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Holiday Rentals in Middletown

The Nest, reconnect with that special someone in our charming birdhouse!

9.6 out of 10, Exceptional, (22)
"Cozy and a great place to stay!"
The price is €158
includes taxes & fees
29 Jun - 30 Jun
The Nest, reconnect with that special someone in our charming birdhouse!

Private Cabin on 90 Acres!

10.0 out of 10, Exceptional, (3)
"We enjoyed our stay in this peaceful cabin, the atmosphere was great for a date nite and the hot tube was very relaxing. "
Private Cabin on 90 Acres!

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

9.4 out of 10, Exceptional, (26)
"Great place to get away from it all. Clean, modern getaway in the woods with a great Jacuzzi."
The price is €174
includes taxes & fees
26 Jun - 27 Jun
Owl house was built for unplugging, relaxing & connecting with friends/family

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

8.8 out of 10, Excellent, (16)
"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.

10.0 out of 10, Exceptional, (16)
"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.

Seclusion at its finest! 90 acres of fredom!

10.0 out of 10, Exceptional, (1)
"Had a great stay in a very secluded area with just one other cabin about 100 yards away. Everything was clean and tidy. Perfect place for privacy and quietness. Hot tub was a plus and used it one time. Super hot outside for us personally but during the fall or early spring, it would be a huge benefit. Washer and dryer was a nice amenity! I do consulting for Toyota and it was only about a 15 minute drive from the casting plant there in Troy Missouri. I definitely recommend this for business...
Seclusion at its finest! 90 acres of fredom!

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

9.6 out of 10, Exceptional, (4)
"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

Cozy custom-built Cabin - Lakeside

10.0 out of 10, Exceptional, (51)
"Perfect place for a retreat. The cabin was very clean and comfortable. Enjoyed the firepit and hot tub overlooking the pond. Definitely will come back."
Cozy custom-built Cabin - Lakeside

New custom-built TREEHOUSE - Sunrise

2.0 star property
10.0 out of 10, Exceptional, (8)
"5 star stay!"
New custom-built TREEHOUSE - Sunrise

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

10.0 out of 10, Exceptional, (24)
"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.

Historic Main Street Cottage

10.0 out of 10, Exceptional, (25)
"Home was very nice; cozy with great character. Nice amenities. Brenda was a wonderful host; very attentive and an excellent communicator."
Historic Main Street Cottage

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

10.0 out of 10, Exceptional, (5)
"Lovely facility, well thought out. Everything we needed."
'Foxes Den' w/ Hot Tub, Pool Table & Fire Pit!

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"

The Venue at Hermann

The Venue at Hermann

Cottage Properties - Country Log Cabin

10.0 out of 10, Exceptional, (162)
"Great hosts, very easy to talk to and accommodate our needs for the weekend. Will definitely book again for next year. "
Cottage Properties - Country Log Cabin

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

The price is €368
includes taxes & fees
6 Jul - 7 Jul
Sweet Retreat at Mark Twain Lake! Historic 4BR/2BA Dog & Family Friendly Home!

4K Ranch - 10 acre property & home near Hermann

10.0 out of 10, Exceptional, (11)
"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, (11)
"We enjoyed our stay at the Chicken Coop! Nice home, very clean and good location for Troy. "
The Chicken Coop on Highway H

The Yellow Rose Historic Home

10.0 out of 10, Exceptional, (11)
"Loved staying at the yellow rose had plenty of room for family was such a nice place"
The price is €277
includes taxes & fees
26 Jun - 27 Jun
The Yellow Rose Historic Home

Sweet Cherry Escape | JZ Vacation Rentals

3.0 star property
The price is €378
includes taxes & fees
7 Jul - 8 Jul
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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Frequently asked questions

Can I find a holiday rental in Middletown?

Yes, there are holiday rentals close to the most popular sights in Middletown, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Middletown has to offer?

Hot Tub and Private Pool, 7 Bedroom, 4 Bathroom Home. Sleeps 16 comfortably.: This holiday home rental outside of Middletown offers an outdoor pool, a patio and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and 1 hot tub.

What’s there to see and do in Middletown?

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

What’s a holiday rental in Middletown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middletown. Holiday rentals provide amenities like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.