Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Dec 12 - Dec 14
In two months
Jan 23 - Jan 25
In three months
Feb 20 - Feb 22
In four months
Mar 20 - Mar 22

Vacation Rentals in Middletown

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

Cabin in Troy

9.4 out of 10, Exceptional, (39)
"Very peaceful and great get place to escape "
United States
Toney D.
The price is ￥26,590
￥32,019 total
includes taxes & fees
Nov 26 - Nov 27
The Nest, reconnect with that special someone in our charming birdhouse!
TV, fireplace, DVD player, stereo
Cottage Properties - Country Log Cabin

Cabin in High Hill

10.0 out of 10, Exceptional, (173)
"Great people, great place. Thanks"
United States
Gary G.
Cottage Properties - Country Log Cabin
Interior
Treehouse - Sunrise

Cabin in Jonesburg

2.0 star property
10.0 out of 10, Exceptional, (20)
"Perfect, peaceful cabin. Everything we needed for a weekend getaway. "
United States
Zane S.
Treehouse - Sunrise
Outdoor pool
Hot Tub and Private Pool, 7 Bedroom, 4 Bathroom Home. Sleeps 16 comfortably.

Vacation Home in Warrenton

8.8 out of 10, Excellent, (20)
"We had a great time at this location. It was cute, clean, and well maintained."
United States
Chloe A.
Hot Tub and Private Pool, 7 Bedroom, 4 Bathroom Home. Sleeps 16 comfortably.
Interior
Owl house was built for unplugging, relaxing & connecting with friends/family

Cabin in Troy

9.4 out of 10, Exceptional, (36)
"Great hosts, great stay, always enjoy my time"
United States
Anonymous traveler
The price is ￥26,590
￥32,019 total
includes taxes & fees
Nov 26 - Nov 27
Owl house was built for unplugging, relaxing & connecting with friends/family
Interior
New - custom-built Treehouse - Twilight

Cabin in Jonesburg

10.0 out of 10, Exceptional, (7)
New - custom-built Treehouse - Twilight
Outdoor spa tub
Seclusion at its finest on 90+ Acres

Cabin in Troy

10.0 out of 10, Exceptional, (5)
"Quiet and lovely, excellent for any one who needs a quiet place to think and rest"
United States
Twixacat E.
Seclusion at its finest on 90+ Acres
Outdoor dining
Secluded 2 bedroom home close to Hermann

Vacation Home in New Florence

9.8 out of 10, Exceptional, (44)
"We thoroughly enjoyed our stay! The house was very clean and spacious for our group of 6. Very happy with our experience!"
United States
Renee R.
The price is ￥28,154
￥39,034 total
includes taxes & fees
Nov 25 - Nov 26
Secluded 2 bedroom home close to Hermann
Property grounds
Historic Main Street Cottage

Vacation Home in Troy

10.0 out of 10, Exceptional, (36)
"Clean, comfortable, and pet friendly. Ideal for our needs. "
United States
Tony P.
Historic Main Street Cottage
Fridge, microwave, oven, stovetop
The Chicken Coop on Highway H

Vacation Home in Troy

10.0 out of 10, Exceptional, (16)
"Great place to stay. Beautiful decor. Peaceful, relaxing, great set up, welcoming. Loved the decor. "
United States
Paul G.
The Chicken Coop on Highway H
Fridge, microwave, oven, stovetop
Welcome to the "Blue House on Boone"

Vacation Home in Troy

10.0 out of 10, Exceptional, (41)
"Great place to stay. Very cozy and owners were quick to respond to any questions we had prior to our arrival and during our stay. Great communication and will book again if we are in the area traveling. "
United States
Emily A.
Welcome to the "Blue House on Boone"
Terrace/patio
Cozy custom-built Cabin - Lakeside

Cabin in Jonesburg

10.0 out of 10, Exceptional, (61)
"AMA ing place! Very clean amazing views quiet relaxing place!!"
United States
Kristina
Cozy custom-built Cabin - Lakeside
Outdoor spa tub
Private Cabin on 90 Acres!

Cabin in Troy

10.0 out of 10, Exceptional, (6)
"We enjoyed our stay in this peaceful cabin, the atmosphere was great for a date nite and the hot tube was very relaxing. "
United States
Anonymous traveler
Private Cabin on 90 Acres!
Interior
A real charmer built in 1915 , pet friendly , located next to Mark Twain lake.

Vacation Home in Perry

10.0 out of 10, Exceptional, (26)
"Clean, comfortable, with a nice backyard for the dogs. Enjoyed our stay."
United States
Patrick S.
A real charmer built in 1915 , pet friendly , located next to Mark Twain lake.
Exterior
Sweet Cherry Escape | JZ Vacation Rentals

Vacation Home in Warrenton

3.0 star property
Sweet Cherry Escape | JZ Vacation Rentals
Smart TV
70's Park Side Cabin with Kayaks

Cabin in Troy

9.8 out of 10, Exceptional, (41)
"It was a cute place to stay "
United States
Jennifer
70's Park Side Cabin with Kayaks
5 bedrooms, desk, travel crib, free WiFi
The Yellow Rose Historic Home

Vacation Home in Louisiana

9.8 out of 10, Exceptional, (12)
"We are 7 sisters aged 50-76. We had a wonderful stay at the Yellow Rose. This beautiful old home had rooms and beds for all of us. Would definitely stay here again"
United States
Ellen B.
The price is ￥34,488
￥49,475 total
includes taxes & fees
Nov 30 - Dec 1
The Yellow Rose Historic Home
1 bedroom, WiFi, bed sheets
The Venue at Hermann

Apartment in Hermann

10.0 out of 10, Exceptional, (4)
"Our stay at the property near Big Sping, MO was excellent. The venue was convenient for us to visit friends near the area. The room was as we expected, clean, bright and convenient. "
United States
Jerry B.
The Venue at Hermann
1 bedroom, WiFi, bed sheets
The Venue at Hermann

Apartment in Hermann

6.0 out of 10, (1)
"Everything was very clean except the cloth couch had some spots on it. Probably needed a fabric cleaner. The main reason for the low stars is the bed was absolutely terrible. It wasn't until the 2nd night that we realized the bed frame was broken. "
United States
Jessica S.
The Venue at Hermann
Smart TV, books
4K Ranch - 10 acre property & home near Hermann

Vacation Home in New Florence

10.0 out of 10, Exceptional, (15)
"We stayed here for a weekend getaway with friends. The property was perfect distance from Hermann and had tons of fun spaces! We can’t wait to stay here again!"
United States
roger l.
4K Ranch - 10 acre property & home near Hermann
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

Cozy custom-built Cabin - Lakeside

Cozy custom-built Cabin - Lakeside

10/10 Excellent
"Beautiful location. There is just enough cell service to send an occasional text and make a phone call if you step outside (att). The water pressure was disappointing after seeing the dual shower heads in the photos but the unlimited hot water allowed us to opt for several relaxing baths instead. My wife loved all the nature and animals. This is a perfect spot for resetting and relaxing. We used the complimentary s'mores and Keurig machine."
Eric W. 3-night trip
Posted 4 days ago
Cozy custom-built Cabin - Lakeside

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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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?

Hot Tub and Private Pool, 7 Bedroom, 4 Bathroom Home. Sleeps 16 comfortably.: This vacation home rental near Middletown offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a hot tub.

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.