Middletown vacation rentals

KAYAK searches hundreds of travel sites at once for vacation home deals in Middletown

Here is why travelers choose KAYAK

Free to useThere are no hidden charges or fees.

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Recommended by KAYAK
Booking Insights
Recommended by KAYAK

Best Middletown vacation rentals

Pet Friendly Home with Fenced in Yard - Middletown - Bedroom
Pet Friendly Home with Fenced in Yard
Middletown, OH
House
Parking
Free Wi-Fi
Pet friendly
$367+
Check availability
Suburban Sanctuary! Convienient to Cincinnati and Dayton - Middletown - Bedroom
Suburban Sanctuary! Convienient to Cincinnati and Dayton
Middletown, OH
9.0Wonderful(32)
House
Free Wi-Fi
$235+
Check availability
Calm & Peaceful 3B: King Beds by Liberty Hospital - Middletown - Dining room
Calm & Peaceful 3B: King Beds by Liberty Hospital
Middletown, OH
7.0Good(1)
House
Free Wi-Fi
$168+
Check availability
Cozy Updated Cottage Style Home near Historic distric in Middletown - Middletown - Kitchen
Cozy Updated Cottage Style Home near Historic distric in Middletown
Middletown, OH
10Wonderful(31)
House
$181+
Check availability
Diamonds are Forever-700 - Middletown - Living room
Diamonds are Forever-700
Middletown, OH
9.6Wonderful(6)
House
Parking
Free Wi-Fi
$369+
Check availability
4 Bed 2.5 Bath Sleeps 10- King of Karincrest - Middletown - Living room
4 Bed 2.5 Bath Sleeps 10- King of Karincrest
Middletown, OH
8.8Very good(16)
House
Free Wi-Fi
$605+
Check availability
Middletown Centenarian 4 Bed 2 Bath Sleeps 12 - Middletown - Building
Middletown Centenarian 4 Bed 2 Bath Sleeps 12
Middletown, OH
8.8Very good(20)
House
Free Wi-Fi
$519+
Check availability
Comfort on the Court 3 Bed 2 Bath Sleeps 6 - Middletown - Living room
Comfort on the Court 3 Bed 2 Bath Sleeps 6
Middletown, OH
8.5Very good(8)
House
Free Wi-Fi
$422+
Check availability
Newly built sanctuary! Come make yourself at home! - Middletown - Kitchen
Newly built sanctuary! Come make yourself at home!
Middletown, OH
9.7Wonderful(17)
House
Free Wi-Fi
$277+
Check availability
Cute Ranch home Middletown, OH - Middletown - Living room
Cute Ranch home Middletown, OH
Middletown, OH
8.0Very good(1)
House
$272+
Check availability
Stanley Cozyside - Middletown - Living room
Stanley Cozyside
Middletown, OH
9.6Wonderful(10)
House
$203+
Check availability
NEW, big, beautiful, Executive Home Liberty Twp - Middletown - Living room
NEW, big, beautiful, Executive Home Liberty Twp
Middletown, OH
10Wonderful(2)
Villa
Free Wi-Fi
$609+
Check availability
Booking Insights

KAYAK’s insights for vacation rentals in Middletown

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Middletown with confidence.

What is the cheapest day of the week to book a vacation rental in Middletown?

Sunday offers the lowest rates in Middletown, with an average nightly price of $151. The highest prices are found on Saturday, with average rates at $380.

Find deals

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

September
June
$217
$312
Cheapest month to stay with an average 32% drop in price.
Most expensive month to stay with an average 24% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Middletown vacation rental deals

  • Vacation rentals in Middletown are around 69% more expensive than hotels on average. Search here to compare prices for all accommodation types in Middletown.
  • The best vacation rental properties in Middletown are Cozy Updated Cottage Style Home near Historic distric in Middletown (10.0, 31 reviews), Suburban Sanctuary! Convienient to Cincinnati and Dayton (9.0, 32), and Middletown Centenarian 4 Bed 2 Bath Sleeps 12 (8.8, 20), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Middletown, you should consider visiting during the low season. The cheapest vacation homes in Middletown can be found in September and October.
  • The cheapest night for renting a vacation home in Middletown is Sunday. In contrast, the most expensive is Saturday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Middletown for 15 days.

FAQs when booking a vacation home in Middletown

  • What types of vacation rentals are available in Middletown?

    There are loads of different property types that you can make your vacation home in Middletown. You’ll find apartments, houses and villas.

  • Are there any pet-friendly vacation rentals in Middletown?

    There are a number of dog and pet-friendly Middletown vacation rentals, with around 15% allowing you to bring your pet along with you.

  • How much is a vacation rental in Middletown for this weekend?

    In the last 72 hours, users have found Middletown vacation rentals for this weekend for as low as $269 per night. Search here for similar prices

  • How can I find vacation rentals near me in Middletown?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Middletown?

Our map will help you find the perfect place to stay in Middletown by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Middletown