Middletown Vacation Rentals

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    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 10 - Oct 12
In two months
Nov 21 - Nov 23
In three months
Dec 19 - Dec 21
In four months
Jan 16 - Jan 18

Vacation Rentals in Middletown

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

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

9.8 out of 10, Exceptional, (32)
"Very peaceful and great get place to escape "
$170 nightly
The price is $181
Sep 29 - Sep 30
Total with taxes and fees
The Nest, reconnect with that special someone in our charming birdhouse!
Owl house was built for unplugging, relaxing & connecting with friends/family
Interior

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

9.4 out of 10, Exceptional, (32)
"Great hosts, great stay, always enjoy my time"
$185 nightly
The price is $197
Sep 30 - Oct 1
Total with taxes and fees
Owl house was built for unplugging, relaxing & connecting with friends/family
New - custom-built Treehouse - Twilight
Interior

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
Interior

Treehouse - Sunrise

2.0 star property
10.0 out of 10, Exceptional, (13)
"5 star stay!"
Treehouse - Sunrise
Cottage Properties - Country Log Cabin
TV, fireplace, DVD player, stereo

Cottage Properties - Country Log Cabin

10.0 out of 10, Exceptional, (167)
"Had a great time! "
Cottage Properties - Country Log Cabin
Hot Tub and Private Pool, 7 Bedroom, 4 Bathroom Home. Sleeps 16 comfortably.
Outdoor pool

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.
Secluded 2 bedroom home close to Hermann
Outdoor dining

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!"
$237 nightly
The price is $250
Sep 29 - Sep 30
Total with taxes and fees
Secluded 2 bedroom home close to Hermann
The Venue at Hermann
1 bedroom, WiFi, bed sheets

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
Terrace/patio

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
Private Cabin on 90 Acres!
1 bedroom, WiFi, bed sheets

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!
The Venue at Hermann
1 bedroom, WiFi, bed sheets

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
Seclusion at its finest on 90+ Acres
Fridge, microwave, oven, stovetop

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
Fridge, microwave, oven, stovetop

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

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!
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. "
$410 nightly
The price is $430
Sep 29 - Sep 30
Total with taxes and fees
Sweet Retreat at Mark Twain Lake! Historic 4BR/2BA Dog & Family Friendly Home!
Welcome to the "Blue House on Boone"
Fridge, microwave, oven, stovetop

Welcome to the "Blue House on Boone"

10.0 out of 10, Exceptional, (38)
"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"
Sweet Cherry Escape | JZ Vacation Rentals
Exterior

Sweet Cherry Escape | JZ Vacation Rentals

3.0 star property
Sweet Cherry Escape | JZ Vacation Rentals
STORMFIELD WEST Country charm nestled in Perry Mo, 3 miles from Mark Twain Lake
Dining

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
Property grounds

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
4K Ranch - 10 acre property & home near Hermann
Smart TV, books

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
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

Super 8 by Wyndham Warrenton

Super 8 by Wyndham Warrenton

10/10 Excellent
"Nice to be able to use Hotel.com when we decide it is time to stop for the night"
Andrew 1-night trip
Posted 6 days ago
Super 8 by Wyndham Warrenton

Find out more about Middletown

Find out more about Middletown

Everything you need to know about Middletown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middletown vacation 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 low season months. For more hustle and bustle, you may prefer to visit Middletown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $181 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown vacation 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 vacation.

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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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.