Title: Middletown Vacation Rentals from CA $281: Short-Term Rentals for 2026 | Expedia.ca

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## Check prices for these dates

In two weeks

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=553248634983107007&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=553248634983107007&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=553248634983107007&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 12 - Jun 14](https://www.expedia.ca/Hotel-Search?regionId=553248634983107007&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Middletown vacation rentals

![Interior](https://images.trvl-media.com/lodging/104000000/103700000/103692500/103692438/529e45ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/104000000/103700000/103692500/103692438/31b86e09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/104000000/103700000/103692500/103692438/25c03e0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/104000000/103700000/103692500/103692438/1049fdd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Troy-Hotels-Owl-House-Was-Built-For-Unplugging.h103692438.Hotel-Information)

Troy

9.4/10

Exceptional

(41 reviews)

"Great stay. Excellent. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Nick V.

CA $232

CA $281 total

includes taxes & fees

Feb 19 - Feb 20

[](https://www.expedia.ca/Troy-Hotels-Owl-House-Was-Built-For-Unplugging.h103692438.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/71000000/70940000/70934000/70933948/f3e09676.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/71000000/70940000/70934000/70933948/54372c0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/71000000/70940000/70934000/70933948/71add150.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/71000000/70940000/70934000/70933948/e07b715a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Secluded 2 bedroom home close to Hermann

[](https://www.expedia.ca/New-Florence-Hotels-Secluded-2-Bedroom-Home-Close-To-Hermann.h70933948.Hotel-Information)

New Florence

9.8/10

Exceptional

(46 reviews)

"Very nice place "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Yaqui S.

CA $245

CA $347 total

includes taxes & fees

Feb 19 - Feb 20

[](https://www.expedia.ca/New-Florence-Hotels-Secluded-2-Bedroom-Home-Close-To-Hermann.h70933948.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/104000000/103700000/103696700/103696614/2434a4a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/104000000/103700000/103696700/103696614/007d641a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/104000000/103700000/103696700/103696614/834ce926.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/104000000/103700000/103696700/103696614/786ebb31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Troy-Hotels-The-Nest.h103696614.Hotel-Information)

Troy

9.4/10

Exceptional

(42 reviews)

"A beautiful tiny house that gave us the opportunity to unplug and get away from the world. Beautiful views yet close enough to town for dinner. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jessica

CA $232

CA $281 total

includes taxes & fees

Feb 19 - Feb 20

[](https://www.expedia.ca/Troy-Hotels-The-Nest.h103696614.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/96000000/95980000/95977000/95976949/a0b541f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/96000000/95980000/95977000/95976949/a454eeca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/96000000/95980000/95977000/95976949/5393ee35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/96000000/95980000/95977000/95976949/1e9bdfd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Yellow Rose Historic Home

[](https://www.expedia.ca/Louisiana-Hotels-The-Yellow-Rose-Historic-Home.h95976949.Hotel-Information)

Louisiana

9.8/10

Exceptional

(12 reviews)

"Loved staying at the yellow rose had plenty of room for family was such a nice place"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Laurie P.

CA $301

CA $433 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Louisiana-Hotels-The-Yellow-Rose-Historic-Home.h95976949.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-03-04&endDate=2026-03-05&regionId=553248634983107007&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## 

The Annual Vacation Sale 

Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

[Book now](https://expedia.ca/deals?rfrr=VR_SPRING_PROMO_553248634983107007)

## Find vacation rentals that suit your style

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Middletown%2C+Missouri%2C+United+States+of+America&regionId=553248634983107007&latLong=39.126986%2C-91.414045&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=APARTMENT)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Middletown%2C+Missouri%2C+United+States+of+America&regionId=553248634983107007&latLong=39.126986%2C-91.414045&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=CABIN)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Middletown%2C+Missouri%2C+United+States+of+America&regionId=553248634983107007&latLong=39.126986%2C-91.414045&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=COTTAGE)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Middletown%2C+Missouri%2C+United+States+of+America&regionId=553248634983107007&latLong=39.126986%2C-91.414045&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=VACATION_HOME)

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## Top Middletown Hotel Reviews

![Luxury Inn & Suites](https://images.trvl-media.com/lodging/47000000/46180000/46170400/46170344/5440936f_y.jpg)

### Luxury Inn & Suites

10/10 Excellent

"Yes"

[](https://expedia.ca/Warrenton-Hotels-Luxury-Inn-Suites.h46170344.Hotel-Information)

![Cozy custom-built Cabin - Lakeside](https://images.trvl-media.com/lodging/79000000/78120000/78113100/78113096/6c0de796_y.jpg)

### Cozy custom-built Cabin - Lakeside

10/10 Excellent

"Everything was perfect! The cabin is beautifully decorated and had everything we needed. The hosts were flexible, gracious and super easy to communicate with. "

[](https://expedia.ca/NEW-Custom-Built-Treehouse-Nestled-In-The-Woods.h78113096.Hotel-Information)

![New - custom-built Treehouse - Twilight](https://images.trvl-media.com/lodging/114000000/113830000/113825200/113825154/d114b929_y.jpg)

### New - custom-built Treehouse - Twilight

10/10 Excellent

"Great experience and place! It had snowed quite a bit the week of our weekend getaway. The tree lined gravel drive had been plowed before our arrival and the privacy the gated entry way and location of the cabin back in the woods was amazing. Hot tub on the deck while the snow fell was magical. Cabin is cozy an it truly achieves the out in nature and away from hectic life calm we were looking for. This will be a repeat trip location for us. Thanks Wendy!"

[](https://expedia.ca/New-Custom-Built-Treehouse-Twilight.h113825154.Hotel-Information)

![Super 8 by Wyndham Warrenton](https://images.trvl-media.com/lodging/1000000/470000/460100/460034/ceec5aac_y.jpg)

### Super 8 by Wyndham Warrenton

10/10 Excellent

"It all went well . Room has been remodeled it was nice ."

[](https://expedia.ca/Warrenton-Hotels-Super-8-By-Wyndham-Warrenton.h460034.Hotel-Information)

![Baymont by Wyndham Warrenton](https://images.trvl-media.com/lodging/1000000/130000/124500/124484/9fa9b759_y.jpg)

### Baymont by Wyndham Warrenton

10/10 Excellent

"Clean rooms , excellent friendly front desk , will use them again "

[](https://expedia.ca/Warrenton-Hotels-Baymont-By-Wyndham-Warrenton.h124484.Hotel-Information)

![Troy Inn and Suites](https://images.trvl-media.com/lodging/33000000/32290000/32284000/32283923/91d634e8_y.jpg)

### Troy Inn and Suites

10/10 Excellent

"Definitely friendly night staff can't say much for the morning staff though they entered my room without permission at 10am checkout wasn't til 11am"

[](https://expedia.ca/Warrenton-Hotels-Troy-Inn-And-Suites.h32283923.Hotel-Information)

![Treehouse - Sunrise](https://images.trvl-media.com/lodging/104000000/103460000/103452200/103452155/38c949ff_y.jpg)

### Treehouse - Sunrise

10/10 Excellent

"Our stay was nothing short of amazing! A true way to unplug from the world. The host thought of everything in these great little tree houses. The host themselves are also amazing! They made themselves very available and accommodating. While we were there it snowed and it was like a winter wonderland. Everywhere you look you are in nature. Whether you are sitting by the fire looking out the windows, sitting at the table eating breakfast, or sitting in the hot tub God's creation is all around you. We are already planning our next trip!"

[](https://expedia.ca/NEW-Custom-Build-Treehouse-Sunrise.h103452155.Hotel-Information)

![Owl house was built for unplugging,  relaxing & connecting with friends/family](https://images.trvl-media.com/lodging/104000000/103700000/103692500/103692438/529e45ac_y.jpg)

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

10/10 Excellent

"Everything was great. Until the biggest snow storm of the year was coming. Had to cut our stay short but would love to come back when weather warms a little. "

[](https://expedia.ca/Troy-Hotels-Owl-House-Was-Built-For-Unplugging.h103692438.Hotel-Information)

![Super 8 by Wyndham Bowling Green](https://images.trvl-media.com/lodging/1000000/870000/861700/861618/d03a723c_y.jpg)

### Super 8 by Wyndham Bowling Green

10/10 Excellent

"No lines, pre-warmedroom "

[](https://expedia.ca/Hannibal-Hotels-Super-8-By-Wyndham-Bowling-Green.h861618.Hotel-Information)

## Find out more about Middletown

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Middletown. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Vacation Homes in Middletown ](https://expedia.ca/Middletown-Private-Vacation-Homes.d553248634983107007-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Middletown ](https://expedia.ca/Middletown-Apartments.d553248634983107007-aaApartments.Travel-Guide-Accommodation)
- [Cabin Rentals in Middletown ](https://expedia.ca/Middletown-Cabins.d553248634983107007-aaCabins.Travel-Guide-Accommodation)
- [Motels in Middletown ](https://expedia.ca/Middletown-Motels.d553248634983107007-aaMotels.Travel-Guide-Accommodation)
- [Farmstay in Middletown ](https://expedia.ca/Middletown-Agritourism.d553248634983107007-aaAgritourism.Travel-Guide-Accommodation)
- [B&B in Middletown ](https://expedia.ca/Middletown-Bed-And-Breakfast.d553248634983107007-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Inns in Middletown ](https://expedia.ca/Middletown-Inns.d553248634983107007-aaInns.Travel-Guide-Accommodation)

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