Middletown Holiday Rentals

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Holiday Rentals in Middletown

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

9.8 out of 10, Exceptional, (32)
"Everything was good, it was a unique experience. Very interesting design "
The price is AU$277
includes taxes & fees
5 Oct - 6 Oct
The Nest, reconnect with that special someone in our charming birdhouse!

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

9.4 out of 10, Exceptional, (33)
"Great hosts, great stay, always enjoy my time"
The price is AU$301
includes taxes & fees
5 Oct - 6 Oct
Owl house was built for unplugging, relaxing & connecting with friends/family

New - custom-built Treehouse - Twilight

10.0 out of 10, Exceptional, (3)
"The twilight cabin was so clean and cozy. We enjoyed our stay. "
New - custom-built Treehouse - Twilight

Treehouse - Sunrise

2.0 star property
10.0 out of 10, Exceptional, (13)
"5 star stay!"
Treehouse - Sunrise

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.

Cottage Properties - Country Log Cabin

10.0 out of 10, Exceptional, (167)
"Had a great time! "
Cottage Properties - Country Log Cabin

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

Cozy custom-built Cabin - Lakeside

10.0 out of 10, Exceptional, (54)
"We really enjoyed our stay. Place is very secluded and had everything we needed for a great weekend away!"
Cozy custom-built Cabin - Lakeside

Seclusion at its finest on 90+ Acres

10.0 out of 10, Exceptional, (4)
"Everything was as advertised. Very nice place"
Seclusion at its finest on 90+ Acres

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

10.0 out of 10, Exceptional, (13)
"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

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!

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 AU$658
includes taxes & fees
6 Oct - 7 Oct
Sweet Retreat at Mark Twain Lake! Historic 4BR/2BA Dog & Family Friendly Home!

Private Cabin on 90 Acres!

10.0 out of 10, Exceptional, (6)
"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!

Welcome to the "Blue House on Boone"

10.0 out of 10, Exceptional, (39)
"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"

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!"
The price is AU$375
includes taxes & fees
13 Oct - 14 Oct
Secluded 2 bedroom home close to Hermann

Sweet Cherry Escape | JZ Vacation Rentals

3.0 star property
Sweet Cherry Escape | JZ Vacation Rentals

The Venue at Hermann

10.0 out of 10, Exceptional, (3)
"The Venue at Herman was an absolute amazing place for our 1st year anniversary!!! Beautiful room!!! So cozy and clean!!! Everything we needed and more!!! We will definitely be telling everyone we know about this place and we will be back again!! "
The Venue at Hermann

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

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
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

Find out more about Middletown

Find out more about Middletown

Everything you need to know about Middletown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middletown holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Middletown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middletown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middletown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middletown holiday rentals we have selected for you start as low as AU$277 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Middletown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middletown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middletown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 New Florence United Methodist Church, Stone Hill Winery and Graham Cave State Park. 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.