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Middletown Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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.
The price is AED 426
AED 755 total
includes taxes & fees
4 Oct - 5 Oct
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, (50 reviews)
"Very nice place "
United States
Yaqui S.
The price is AED 661
AED 936 total
includes taxes & fees
5 Oct - 6 Oct
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, (54 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 AED 624
AED 759 total
includes taxes & fees
4 Oct - 5 Oct
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.
The price is AED 632
AED 1,445 total
includes taxes & fees
29 Oct - 30 Oct
Historic 2BR Home in Downtown Troy - King Bed, Fire Table & Patio
A spacious room with hardwood flooring, a grand piano, a comfortable armchair, and a chandelier.

5. 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 AED 909
AED 1,348 total
includes taxes & fees
4 Oct - 5 Oct
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.

6. 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
The price is AED 1,025
AED 1,669 total
includes taxes & fees
2 Nov - 3 Nov
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

Holiday Inn Express Warrenton by IHG

Holiday Inn Express Warrenton by IHG

10/10 Excellent
"Stay was great. Room was great. Water pressure in the shower is super strong maybe different shower heads would be nice. Breakfast was acceptable. Perhaps extending it to 9:30am would be my suggestion. Staff was great and very friendly. Defiantly would stay again."
miken 2-night trip
Posted 1 day ago
Holiday Inn Express Warrenton by IHG

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.