Middletown Holiday Rentals from €168: Search Short-Term Rentals

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Holiday Rentals in Middletown

"This is our second time staying at this property. Love the seclusion and peacefulness of being in the woods but still a short drive to shops and restaurants. "

"Beautiful views"

includes taxes & fees

27 Nov - 28 Nov

"This was our first time staying at a place like this so we had no idea what to expect or what we needed and and didn't need to bring. Everything was awesome! The host had all the bases covered. The setting is beautiful and was perfect for relaxing. We will definitely be back in the future. It was a great experience. "

"Very comfortable place, we enjoyed our weekend stay. Would go back again."

includes taxes & fees

27 Nov - 28 Nov

"Excellent property.Very clean and comfortable. Stayed for a wedding in town and the house exceeded our expectations. The property owner was very communicative but wasn't in the least bit intrusive. Would highly recommended!!"

"I have stayed here once before and it does not disappoint. It is my “go-to” home when visiting my son and family in Perry. "

"Very cute, cozy, and relaxing. Hot tub was nice! Could use some bug spray to remove wasp and lady bugs. Overall was nice. "

includes taxes & fees

27 Nov - 28 Nov

"Quiet, comfortable stay between Hermann and I-70.Well equipped kitchenette with fridge-freezer, sofa, and smart TV. Could see coming back for a loner visit. "

"My family and I enjoyed our stay. Location is great. We were going to the St. Louis but wanted a quieter area to stay and this place did not disappoint. Serene locale yet mere minutes away from Troy and its numerous amenities. No issues, would recommend to anyone looking for a place to stay in the area."

"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!"

"Lovely facility, well thought out. Everything we needed."

"Me and family stayed here for the weekend since it was close to my daughter's wedding venue. It was perfect for our stay. Lots of space and my husband just adored it. The location, the decor....I think he was ready to move in. LOL Rachel Daugherty "

"Our family had the best time staying in the Yellow Rose! We loved the restored character and mansion feel. There's room for everyone, 2 pianos, lots of board games, a Wii, and a projector for movies. The kitchen was fitted with modern appliances and the tankless water heater means we never ran out of hot water. Comfortable beds too. The game room upstairs was our favorite spot. Carrie is always a pleasure to talk to and she did a great job communicating. Also her tips for places to go were...

includes taxes & fees

1 Dec - 2 Dec

"We meet frie n "

"We stayed at this house the weekend of our wedding and it was perfect! "

"3 couples stayed comfortably while on vacation within minutes of MarkTwain Lake! The Host was always quick to respond and even checked in on us."

"Our stay in Hermann was great and the property was exactly as advertised. Check in/out was very easy. I just have a couple of notes/suggestions. The kitchenette water did not work (it really did not impact our stay as we did not use it. Just wanted to give a heads up). We wished there had been shampoo/conditioner and hairdryer supplied. A suggested improvement would be to install an electric fireplace. I think it would really add to the ambiance of the room. Would definitely recommend...

"The Venue at Hermann was located just out of town from Main Street In Hermann MO, which is just what we were looking for to get away from all the hustle and bustle of the city we live in. The room was very clean and comfortable. Very relaxing and peaceful place to stay. We Loved it.!! "

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Other types of properties in Middletown you may be interested in

"Friendly staff . quick check in , clean , good breakfast (many choices)."

includes taxes & fees

2 Dec - 3 Dec

"Great location, friendly staff, quiet room, clean and comfortable bed. Hot, delicious breakfast."

includes taxes & fees

3 Dec - 4 Dec

In-room safe, desk, laptop workspace, blackout curtains

"We stayed on the weekend of Diwali (the beginning of the Hindu fiscal year), so we understood the hotel was short staffed due to the celebration. On our 3rd attempt at a clean room, we got one. The woman working at check in was very kind. Later that evening when we returned, our TV didn't work. Another lady at the front desk came up and called the owner who walked her through fixing it. The room was clean, the beds were comfortable, and we slept well. The next morning my biggest issue was there...

includes taxes & fees

30 Nov - 1 Dec

Find out more about Middletown

Everything you need to know about Middletown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middletown holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middletown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middletown. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middletown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middletown holiday rentals we have selected for you start as low as €168 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Middletown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middletown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middletown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Recent reviews of Middletown properties

5/5 Excellent

Much needed quiet time

"This was our first time staying at a place like this so we had no idea what to expect or what we needed and and didn't need to bring. Everything was awesome! The host had all the bases covered. The setting is beautiful and was perfect for relaxing. We will definitely be back in the future. It was a great experience. "

A verified traveller stayed at Cottage Properties - Country Log Cabin

Posted 2 days ago

5/5 Excellent

Main St. Troy. Wonderful Home!!

"Excellent property.Very clean and comfortable. Stayed for a wedding in town and the house exceeded our expectations. The property owner was very communicative but wasn't in the least bit intrusive. Would highly recommended!!"

A verified traveller stayed at Historic Main Street Cottage

Posted 9 days ago

5/5 Excellent

Will stay again, very lovely overall & kind people

"Fenil was amazing and friendly and very courteous and accomodating. I was unaware there is no elevator & we were on the second floor. He immediately offered to move us to the ground floor. The accomodations were very clean with one spot on the tissue holder. On the bed coverlet there were some stains. I know they recently took over ownership and are working to improve the entire hotel; it shows! Every employee I encountered was very courteous. The bathroom was spotlessly clean. Same with the sink area. The amenities, soaps, etc. were lovely. In room was a just a little larger than mini fridge and a small microwave, perfectly sized. There was a very nice table with 2 chairs in the room, perfect for our needs. Only one side of the bed had outlets. It appears the bed used to be positioned closer to the outside wall where there would have been outlets on both sides of the bed. The positioning of the bed now is actually better and makes the room appear even larger, which is saying something as the room is large! For view I put "mountain view" because there was not an option for "country view". There are no actual mountains. The hotel is just far enough away from the roundabout and freeway to be free of road noise. There was a safe in the room, and switches for both the light and fan inside the bathroom. I mention this bc I was in a much larger chain hotel 3 days prior that had neither of those. Will stay next time we travel there. "

A verified traveller stayed at Knights Inn New Florence

Posted 9 days ago

5/5 Excellent

"I would give 10 stars if I could. I was foolish and left my computer in the room and then drove away. They notified me upon finding it. Kept in touch and sent the machine as soon as they could. I am using it now. The room was clean. The staff was wonderful. The water was hot. There is a place to eat next door. Oh yes, the Mississippi was beautiful too. We could walk down to the water's edge. Yes."

A verified traveller stayed at River's Edge Motel

Posted 1 month ago

Frequently asked questions

Can I find a holiday rental in Middletown?

Yes, there are holiday rentals close to the most popular sights in Middletown, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Middletown has to offer?

A real charmer built in 1915 , pet friendly , located next to Mark Twain lake.: This holiday home rental outside of Middletown is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

What’s there to see and do in Middletown?

While exploring the area, visit the sights like Stone Hill Winery, Graham Cave State Park and New Florence United Methodist Church. In the wider area, you’ll also find Curling Vine Winery.

What’s a holiday rental in Middletown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middletown. Holiday rentals provide amenities like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.

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Holiday Rentals in Middletown

Check Middletown holiday rental availability

Holiday Rentals in Middletown

Cozy custom-built cabin - Lakeside

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

Cottage Properties - Country Log Cabin

Secluded 2 bedroom home close to Hermann

Historic Main Street Cottage

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

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

The Venue at Hermann

70's Park Side Cabin with Kayaks

4K Ranch - 10 acre property & home near Hermann

Troy Apartment w/ Hot Tub, Pool Table + Fire Pit!

The Venue at Hermann

Relaxing, Quiet get away where you can enjoy the outdoors.

The Yellow Rose Historic Home

Sweet Cherry Escape by JZ Vacation Rentals

Welcome to the "Blue House on Boone"

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

The Venue at Hermann

The Venue at Hermann

The Venue at Hermann

Other types of properties in Middletown you may be interested in

Baymont by Wyndham Warrenton

Holiday Inn Express Warrenton, an IHG Hotel

Super 8 by Wyndham Warrenton

Find out more about Middletown

Recent reviews of Middletown properties

Cottage Properties - Country Log Cabin

Baymont by Wyndham Warrenton

Cozy custom-built cabin - Lakeside

Holiday Inn Express Warrenton, an IHG Hotel

Historic Main Street Cottage

Secluded 2 bedroom home close to Hermann

Knights Inn New Florence

Luxury Inn & Suites

River's Edge Motel

Frequently asked questions