Middletown Vacation Rentals

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Our top choices for Middletown vacation rentals

Vacation Home in Middletown

Papa's Cabin - 40 acres & 5 acre lake!
10.0 out of 10, Exceptional, (1 review)
"This place was seriously a slice of heaven. The hosts were very attentive and welcoming! The house was fully stocked with anything we may have needed, we will definitely be back!"
United States
Kylee F.
$200 nightly
The price is $209
Mar 10 - Mar 11
Total with taxes and fees
Papa's Cabin - 40 acres & 5 acre lake!
9.4 out of 10, Exceptional, (43 reviews)
"Great stay. Excellent. "
United States
Nick V.
$193 nightly
The price is $206
Mar 8 - Mar 9
Total with taxes and fees
Owl house was built for unplugging, relaxing & connecting with friends/family

Vacation Home in New Florence

Secluded 2 bedroom home close to Hermann
9.8 out of 10, Exceptional, (46 reviews)
"Very nice place "
United States
Yaqui S.
$237 nightly
The price is $253
Mar 8 - Mar 9
Total with taxes and fees
Secluded 2 bedroom home close to Hermann

Vacation Home in Louisiana

The Yellow Rose Historic Home
9.8 out of 10, Exceptional, (12 reviews)
"Loved staying at the yellow rose had plenty of room for family was such a nice place"
United States
Laurie P.
$306 nightly
The price is $331
Mar 9 - Mar 10
Total with taxes and fees
The Yellow Rose Historic Home
9.4 out of 10, Exceptional, (42 reviews)
"A beautiful tiny house that gave us the opportunity to unplug and get away from the world. Beautiful views yet close enough to town for dinner. "
United States
Jessica
$193 nightly
The price is $206
Mar 8 - Mar 9
Total with taxes and fees
The Nest, reconnect with that special someone in our charming birdhouse!
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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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 $206 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 Stone Hill Winery, Graham Cave State Park, and New Florence United Methodist Church. 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.