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Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Middletown vacation rentals

Living area

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, (47 reviews)
"Was very clean, great little spot for a weekend get away. Was everything they said it was."
United States
Dillon E.
The price is ￥27,560
￥33,511 total
includes taxes & fees
Jul 21 - Jul 22
The Nest, reconnect with that special someone in our charming birdhouse!
Interior

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 ￥18,806
￥33,308 total
includes taxes & fees
Aug 4 - Aug 5
Papa's Cabin - 40 acres & 5 acre lake!
Outdoor dining

Secluded 2 bedroom home close to Hermann

Secluded 2 bedroom home close to Hermann
New Florence
9.8 out of 10, Exceptional, (47 reviews)
"Very nice place "
United States
Yaqui S.
The price is ￥29,182
￥40,968 total
includes taxes & fees
Jul 19 - Jul 20
Secluded 2 bedroom home close to Hermann
Dining

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 ￥28,371
￥63,358 total
includes taxes & fees
Aug 9 - Aug 10
Historic 2BR Home in Downtown Troy - King Bed, Fire Table & Patio
Living area

Perfect new construction apartment centrally located in Troy.

Perfect new construction apartment centrally located in Troy.
Troy
The price is ￥25,534
￥44,676 total
includes taxes & fees
Jul 22 - Jul 23
Perfect new construction apartment centrally located in Troy.
Interior

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.
The price is ￥41,584
￥60,753 total
includes taxes & fees
Jul 23 - Jul 24
The Yellow Rose Historic Home
Fridge, microwave, oven, stovetop

Cozy Cottage on 12 tranquil acres in Wright City, Mo. Minutes to wedding venues!

Cozy Cottage on 12 tranquil acres in Wright City, Mo. Minutes to wedding venues!
Wright City
The price is ￥51,068
￥84,684 total
includes taxes & fees
Jul 21 - Jul 22
Cozy Cottage on 12 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

Extended Stay Warrenton Inn

Extended Stay Warrenton Inn

10/10 Excellent
"For a cheaper hotel room for the area the place was pretty nice. I’m sure why people are leaving reviews about not getting their $1.50 back, if that’s the case they probably shouldn’t be traveling. The front desk person was upfront with me about having visitors and pets and none of that was a problem. Great place if you plan on just needing a place to stay for the night or don’t expect all the amenities as higher end hotels. Would stay again!"
Matthew 1-night trip
Posted 1 day ago
Extended Stay Warrenton Inn

Find out more about Middletown

Search for holiday rentals in Middletown on Expedia! You can easily find your home rentals, villas, holiday apartments in Middletown using one of the methods below:

  • View our selection of featured holiday rentals in Middletown
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  • Enter your travel dates to view the best deals on holiday rentals in Middletown while they last

Look no further and take a look at our great range of rental properties in Middletown!

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 Curling Vine Winery. In the larger area, you’ll also find Stone Hill 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.