Middletown Vacation Rentals

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Our top choices for Middletown vacation rentals

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

Papa's Cabin - 40 acres & 5 acre lake!
Middletown
10.0 out of 10, Exceptional, (2 reviews)
"We absolutely loved our stay at the cabin!! So much space to spread out inside, and the property & lake are so peaceful and enjoyable to explore. Though we only spent one night, we really loved it there, and will definitely be back when we are in the area visiting family!"
United States
Scott V.
The price is CA $167
CA $292 total
includes taxes & fees
Jun 2 - Jun 3
Papa's Cabin - 40 acres & 5 acre lake!

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

The Nest, reconnect with that special someone in our charming birdhouse!
Troy
9.4 out of 10, Exceptional, (45 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
The price is CA $234
CA $284 total
includes taxes & fees
Jun 2 - Jun 3
The Nest, reconnect with that special someone in our charming birdhouse!

Secluded 2 bedroom home close to Hermann

Secluded 2 bedroom home close to Hermann
New Florence
9.8 out of 10, Exceptional, (46 reviews)
"Very nice place "
United States
Yaqui S.
The price is CA $248
CA $351 total
includes taxes & fees
Jun 2 - Jun 3
Secluded 2 bedroom home close to Hermann

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

Historic 2BR Home in Downtown Troy - King Bed, Fire Table & Patio
Troy
The price is CA $283
CA $603 total
includes taxes & fees
Jun 30 - Jul 1
Historic 2BR Home in Downtown Troy - King Bed, Fire Table & Patio

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

Owl house was built for unplugging, relaxing & connecting with friends/family
Troy
9.4 out of 10, Exceptional, (46 reviews)
"We had a great weekend getaway. It was good to relax and have some family time. "
United States
Christopher W.
The price is CA $234
CA $284 total
includes taxes & fees
Jun 2 - Jun 3
Owl house was built for unplugging, relaxing & connecting with friends/family

The Yellow Rose Historic Home

The Yellow Rose Historic Home
Louisiana
9.8 out of 10, Exceptional, (17 reviews)
"Beautiful place for a family gathering! The kitchen had everything we needed for our meals. The host was kind and welcoming, and the unique historic home was grand and comfortable, with a lot of things for the youngsters to marvel at! We’ll be returning soon! "
United States
Theresa
The price is CA $341
CA $503 total
includes taxes & fees
Jun 14 - Jun 15
The Yellow Rose Historic Home
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Middletown. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.