Middletown Vacation Rentals from ￥22,041: Search Short-Term Rentals

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Vacation Rentals in Middletown

Our top choices for Middletown vacation rentals

"Everything was good, it was a unique experience. Very interesting design "

￥26,922 total

includes taxes & fees

Aug 24 - Aug 25

"We had a great time at this location. It was cute, clean, and well maintained."

"Responses from the owners were swift, the home was beautiful, the morning cows made the morning much brighter, all the necessities needed for the stay inside the home were there. The bedding was nice and comfy, the coffee bar and board game options were lovely. 10/10 would recommend this location. "

"Had a great time! "

"We enjoyed every minute in this charming home It was very clean and came with everything we needed I will be back Chris was very helpful and quick to respond to all my questions "

"Everything is beautiful and peaceful. Highly recommend to anyone. "

￥29,439 total

includes taxes & fees

Aug 27 - Aug 28

"5 star stay!"

"Check in was easy. plenty of room for the 10 of us. "

"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. "

"Super cute little cabin with a great atmosphere, cute and homey feel with an amazing view"

"The house was great - just as advertised, safe, quiet. A real architectural gem. We had 7 and a puppy and it all worked out great. Loved the patio and fire pit. "

￥62,891 total

includes taxes & fees

Aug 24 - Aug 25

"Quiet and lovely, excellent for any one who needs a quiet place to think and rest"

"The house was nice and convenient for spending time with family."

5 bedrooms, desk, travel crib, free WiFi

"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"

￥46,186 total

includes taxes & fees

Aug 24 - Aug 25

"We enjoyed our stay at the Chicken Coop! Nice home, very clean and good location for Troy. "

"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!"

"We only had a short stay, but it was very nice. Such a cute, secluded place right outside of Herman. Worked out perfect for our winery tour. "

￥37,165 total

includes taxes & fees

Aug 24 - Aug 25

"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. "

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Top Middletown Hotel Reviews

Baymont by Wyndham Warrenton

10/10 Excellent

"Pretty hotel. The pool was great. Porch outside of the pool for bbqs and hanging out"

Cottage Properties - Country Log Cabin

10/10 Excellent

"We absolutely loved my stay at this property! It was a perfect blend of relaxation and activity, with so much to do right on-site. We found plenty of ways to unwind while also enjoying various activities. The peaceful atmosphere made it easy to escape the daily grind. The owners are great people. It was our anniversary and they gave us a bottle of wine to celebrate with. "

Knights Inn New Florence

10/10 Excellent

"I really enjoyed staying at this hotel. I don’t really understand why it doesn’t have a lot of stars. I don’t think this hotel had room service but there’s a couple restaurants and gas station for food and drinks not even 2 minutes down the street. I missed breakfast ,unfortunately, but it looked like the guests got to make their own Belgian waffle so I missed out. I mainly enjoyed how homey and cozy the hotel felt and the beds were pretty comfortable but that’s just my personal preference. And the shower water stayed consistently hot which that’s seems to be an issue with a lot of other hotels but not this one. I definitely believe it’s a great hotel for $89 for 4 people for one night. "

Private Cabin on 90 Acres!

10/10 Excellent

"Peaceful and relaxing stay. Beautiful inside, welll designed and the bed was VERY comfortable! Hot tub was an absolute plus!! The only recommendation I would have was to have a sand entryway to the pond so you can float around and easy access for the kayaks. We will will be back!! "

A real charmer built in 1915 , pet friendly , located next to Mark Twain lake.

10/10 Excellent

"Very convenient for anyone visiting Mark Twain. Plenty of space, large fenced backed yard for your furry friends, & many conveniences to make your stay enjoyable. No need to stock up on groceries as there is a grocery right next door. Fire up one of the two provided bbq pits & enjoy the covered patio area with a table for 6."

Find out more about Middletown

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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 New Florence United Methodist Church, Stone Hill Winery, and Graham Cave State Park. 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.

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Middletown Vacation Rentals

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Vacation Rentals in Middletown

Our top choices for Middletown vacation rentals

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

Hot Tub and Private Pool, 7 Bedroom, 4 Bathroom Home. Sleeps 16 comfortably.

DairyLand - A Private Getaway on 16 acres next door to Dairy Farm with EV Hookup

Cottage Properties - Country Log Cabin

A real charmer built in 1915 , pet friendly , located next to Mark Twain lake.

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

New custom-built TREEHOUSE - Sunrise

Private Cabin on 90 Acres!

STORMFIELD WEST Country charm nestled in Perry Mo, 3 miles from Mark Twain Lake

Welcome to the "Blue House on Boone"

New - custom-built Treehouse - Twilight

Cozy custom-built Cabin - Lakeside

Sweet Retreat at Mark Twain Lake! Historic 4BR/2BA Dog & Family Friendly Home!

Seclusion at its finest on 90+ Acres

70's Park Side Cabin with Kayaks

The Yellow Rose Historic Home

The Chicken Coop on Highway H

4K Ranch - 10 acre property & home near Hermann

Secluded 2 bedroom home close to Hermann

The Venue at Hermann

Top Middletown Hotel Reviews

Baymont by Wyndham Warrenton

The Junction Inn

Cottage Properties - Country Log Cabin

Knights Inn New Florence

River's Edge Motel

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

Private Cabin on 90 Acres!

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

A real charmer built in 1915 , pet friendly , located next to Mark Twain lake.

Find out more about Middletown

Frequently asked questions