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Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Middletown vacation rentals

A laundry area with washing machines, a wooden cabinet, and a bar stool area.

1. Papa's Cabin - 40 acres & 5 acre lake!

Papa's Cabin - 40 acres & 5 acre lake!
Middletown
10.0 out of 10, Exceptional, (4 reviews)
"Overall stay was amazing! The property was just like described and the hostess was easy to communicate with."
United States
Prisilla B.
$197 nightly
The price is $205
Oct 19 - Oct 20
Total with taxes and fees
Papa's Cabin - 40 acres & 5 acre lake!
A covered patio with a table and chairs, a grill, and a view of a grassy yard.

2. Secluded 2 bedroom home close to Hermann

Secluded 2 bedroom home close to Hermann
New Florence
9.8 out of 10, Exceptional, (52 reviews)
"Very nice place "
United States
Yaqui S.
$239 nightly
The price is $255
Oct 19 - Oct 20
Total with taxes and fees
Secluded 2 bedroom home close to Hermann
A cozy living room with a brown leather couch, a wooden spiral staircase, and large windows offering a view of the outdoors.

3. The Nest, unplug& reconnect with that special someone in our charming birdhouse!

The Nest, unplug& reconnect with that special someone in our charming birdhouse!
Troy
9.4 out of 10, Exceptional, (55 reviews)
"The property was amazing perfect for a couple or a individual how wants to unplug."
United States
Jess H.
$195 nightly
The price is $208
Oct 20 - Oct 21
Total with taxes and fees
The Nest, unplug& reconnect with that special someone in our charming birdhouse!
A dining area with a round table and chairs, a bench, and a painting on the wall.

4. Historic 2BR Home in Downtown Troy - King Bed, Fire Table & Patio

Historic 2BR Home in Downtown Troy - King Bed, Fire Table & Patio
Troy
10.0 out of 10, Exceptional, (1 review)
"We came in town for the fair and this place was a very beautiful place. Very clean and very well decorated. It was the perfect place to stay in Troy. The host was very nice and could be reached instantly if we had any issues."
United States
Unspecified B.
$349 nightly
The price is $378
Oct 22 - Oct 23
Total with taxes and fees
Historic 2BR Home in Downtown Troy - King Bed, Fire Table & Patio
A living room with a sofa set, a coffee table, and a TV.

5. Hickory Lake House

Hickory Lake House
3.0 star property
Wright City
$411 nightly
The price is $439
Oct 24 - Oct 25
Total with taxes and fees
Hickory Lake House
A spacious room with hardwood flooring, a grand piano, a comfortable armchair, and a chandelier.

6. The Yellow Rose Historic Home

The Yellow Rose Historic Home
Louisiana
9.8 out of 10, Exceptional, (19 reviews)
"Everything was great!"
United States
Brendan R.
$336 nightly
The price is $364
Oct 19 - Oct 20
Total with taxes and fees
The Yellow Rose Historic Home
A bedroom with a bed, a chair, a ceiling fan, a window with curtains, a mirror, and a nightstand with a lamp.

7. Cozy Cottage on 9 tranquil acres in Wright City, Mo. Minutes to wedding venues!

Cozy Cottage on 9 tranquil acres in Wright City, Mo. Minutes to wedding venues!
Wright City
$428 nightly
The price is $454
Nov 2 - Nov 3
Total with taxes and fees
Cozy Cottage on 9 tranquil acres in Wright City, Mo. Minutes to wedding venues!
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

Bay Inn & Suites Troy

Bay Inn & Suites Troy

8/10 Good
"The room was clean and comfortable"
Donna 1-night trip
Posted 1 day ago
Bay Inn & Suites Troy

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 $205 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.

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?

Papa's Cabin - 40 acres & 5 acre lake!: This Middletown vacation home rental is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

What’s there to see and do in Middletown?

While exploring the area, visit the sights like Graham Cave State Park, New Florence United Methodist Church, and Stone Hill Winery. 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.