Middletown vacation rentals

We found 41 vacation rentals — enter your dates for availability

Discover a selection of 16 homes, 11 apartments, and other vacation rentals in Middletown that are perfect for your trip. Vacation homes provide the best amenities for you and your friends, family, or even pets, such as parking and a pool. At the end of the day, you'll find a rental for everyone's needs, including a place that is accessible or non-smoking.
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more
  • More for less

    More space, more privacy, more amenities — more value
  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Middletown

Why visit Middletown

  1. Diverse Attractions: Experience a mix of urban parks, caves, and historic houses that cater to all interests.
  2. Family-Friendly Activities: Enjoy a variety of fun experiences perfect for families, ensuring everyone has a great time.
  3. Outdoor Adventures: Engage in numerous outdoor activities that allow for exploration and connection with nature.
  4. Charming Neighborhoods: Discover vibrant areas filled with friendly locals, offering a welcoming atmosphere for relaxation.
  5. Budget-Friendly Options: Find affordable accommodations and dining experiences that fit different travel budgets.

Top attractions in and around Middletown

Middletown, Louisville, Kentucky, is perfect for family, business, and outdoor vacations. Visitors can explore a variety of attractions, including urban parks, caves, and historic houses. With options catering to outdoor enthusiasts and families seeking a city experience, Middletown offers a diverse range of activities to enjoy, making it an ideal destination for travelers looking to immerse themselves in both nature and history.

  1. E.P. Tom Sawyer State Park: This urban park features scenic trails, picnic areas, and sports facilities, perfect for family outings and outdoor activities. Enjoy a relaxing day surrounded by nature just 3 miles from Middletown.
  2. Southeast Christian Church: A vibrant community hub, this church offers a rich cultural experience, showcasing engaging services and events that foster connection and spirituality right in Middletown.
  3. Louisville Mega Cavern: An expansive underground adventure park located 10 miles away, it offers zip-lining, tram tours, and a unique glimpse into a former limestone cavern, providing thrilling outdoor fun.

Things to do recommended for couples

For a romantic getaway in Middletown, explore the luxury of Valhalla Golf Club, enjoy live music at Headliners Music Hall, or savor delightful wines at Talon Winery. Each venue offers a unique atmosphere perfect for couples seeking memorable experiences together.

Things to do recommended for families

Families visiting Middletown can enjoy ice skating at IceLand Sports Complex, just 2 miles away, experience thrilling karting at Bluegrass Indoor Karting 3 miles away, and embark on a fun adventure at Danger Run, located 2 miles from Middletown. Exciting activities await everyone!

What do I need to keep in mind when booking a vacation around Middletown

If you're traveling with a group, family, pets, or planning for an extended stay, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Middletown with a group: Think about how many bedrooms you'll require, as well as additional features like a fully equipped kitchen or outdoor space for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Middletown with young kids: Traveling with young kids can be a bit daunting. It’s important to prioritize their comfort and safety, along with ensuring access to suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Middletown: For many families, a vacation isn’t truly fulfilling unless their furry companion is along for the ride. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Middletown: If you're in search of vacation rentals with special offers for month-long stays or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Additionally, think about including amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay near Middletown

Middletown, Louisville, offers a delightful blend of family-friendly activities, vibrant neighborhoods, and outdoor adventures. Visitors can explore nearby areas that exude a welcoming atmosphere, perfect for both relaxation and recreation. With options for budget-friendly stays and a variety of dining experiences, Middletown is ideal for families and business travelers alike. Discover charming parks, friendly locals, and unique attractions that make this charming neighborhood a fantastic destination for your vacation.

  • Woodland Hills: Nestled just 0.7 miles from Middletown, Woodland Hills is a charming village that offers a delightful escape for families and outdoor enthusiasts alike. With its beautiful scenery and welcoming atmosphere, visitors can enjoy recreational areas and pristine golf courses. The local parks and lakes provide ample opportunities for hiking, picnicking, or simply soaking in the natural beauty. Woodland Hills is perfect for those looking to unwind and connect with nature while still being close to urban amenities.
  • Anchorage: Located a mile away from Middletown, Anchorage is a vibrant neighborhood known for its family-friendly environment and urban conveniences. Shoppers will appreciate the well-appointed shopping mall and various retail centers, while golf lovers can enjoy the local courses. Anchorage also boasts beautiful urban parks and serene lakes, making it an ideal spot for outdoor activities. Whether you're attending a conference or simply exploring the area's delightful charm, Anchorage offers a balanced mix of city life and natural beauty.
  • Douglass Hills: Situated 1 mile from Middletown, Douglass Hills is a picturesque village that emphasizes outdoor recreation and community spirit. With its private country clubs and well-maintained golf courses, it’s a haven for sports enthusiasts. Visitors can explore the local urban parks and event venues that frequently host exciting gatherings. Douglass Hills appeals to families looking for a friendly, active atmosphere while still enjoying easy access to nearby urban attractions. It’s a great destination for those seeking both relaxation and adventure.

Best time to go to Middletown

If you're planning a trip to Middletown, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in March and June to July, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancy
January33.1°F (0.6°C)Light RainMostly CloudyAverage
February36.5°F (2.5°C)Light RainMostly CloudyAverage
March46.2°F (7.9°C)Light RainMostly CloudySlightly High
April55.6°F (13.1°C)Light RainMostly SunnyAverage
May65.7°F (18.7°C)Light RainMostly SunnyAverage
June73.9°F (23.3°C)Light RainMostly SunnySlightly High
July77.2°F (25.1°C)Light RainMostly SunnySlightly High
August75.6°F (24.2°C)Light RainMostly SunnyAverage
September69.8°F (21.0°C)Light RainMostly SunnyAverage
October58.1°F (14.5°C)Light RainMostly SunnySlightly Low
November45.9°F (7.7°C)Light RainMostly SunnySlightly Low
December38.8°F (3.8°C)Light RainMostly CloudySlightly Low

Booking with Vrbo is a breeze

Are you hoping to save money on your upcoming trip? Being flexible with your travel dates can be beneficial, as prices often fluctuate. Additionally, booking a longer stay can lead to considerable savings. To discover a Vrbo property that aligns with your budget, utilize our filters to sort by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your total booking. Being the planner truly has its perks! When you join our travel rewards program, One Key, you'll gain access to exclusive discounts and earn OneKeyCash™ on eligible bookings. Sign up today and begin enjoying your savings!

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers an easy-to-use platform for planning your travel. You can start new trips, pick up from where you last left off, or manage your existing plans all in one place. Your saved or booked properties are organized into categories like Potential, Upcoming, or Current Trips for your convenience. To begin using Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

How to get to and around Middletown

The nearest airport is in Louisville Intl. Airport (SDF), located 12.1 mi (19.4 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to Louisville, KY (LOU-Bowman Field), which is 7.4 mi (11.9 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Middletown?
Condos are the most popular kind of vacation rental in Middletown, according to our data. Even if you've got something bigger or smaller in mind, Vrbo has properties in loads of sizes and shapes. Explore our options to find your ideal match.
How much does it cost to rent a vacation rental in Middletown?
The average price for a vacation home in Middletown is determined by a number of factors, like property type, length of stay and season. Whether you'd like a sprawling villa with space for the whole family or an apartment that's perfect for two, just enter your dates of travel to see stays with terrific value.
How much does it cost to rent a beach house in Middletown?
The average price for a vacation rental near the beach in Middletown depends on when you're visiting the area and the size and style of property you want. Find prices quickly and easily on Vrbo by entering your preferred travel dates. Then use our filters to select the number of bedrooms and amenities that you require, like air conditioning, WiFi and a hot tub.
Are there pet-friendly vacation rentals in Middletown?
With 18 vacation rentals that welcome pets, your happy hound can join in on your Middletown break. Use the filter tool to search our pet-friendly vacation rentals and find your pawfect pad on Vrbo.
Can I rent a house with a pool in Middletown?
Grab your swimwear and inflatable unicorn, because there are seven houses with a private pool in Middletown. Stay at one of these terrific vacation rentals and you'll enjoy pool days every day. Simply enter your dates into Vrbo, then use the "pool" filter to find the ideal place for a splashing good time!
What are popular rental amenities in Middletown?
Some of the most popular rental amenities people are searching for in Middletown include a garden, a barbecue grill and a sauna. Whether you're taking a trip with family, friends or even pets, Vrbo vacation homes include the best amenities for chilling out with the people you love.
Are there large group vacation rentals in Middletown?
With two properties that can host 10 people or more in Middletown, you won't have to leave anyone off your guest list. From fun family get-togethers to events like anniversary parties and weddings, Vrbo can help you find a large group rental that fits the occasion.
Are there vacation rentals in Middletown that welcome kids?
Gather your whole family for a memorable adventure in Middletown at one of our 18 family-friendly vacation rentals. Lots of these stays feature conveniences that are perfect for getaways with the little ones, like kitchens, bunk beds and entertainment units. Just check the "Properties good for families" filter and choose your favorite option.
What are the top attractions for families in Middletown?
Keep the kids happy at these fantastic family-friendly attractions in Middletown:

  • Southeast Christian Church
  • Eastgate Shopping Center
  • Village Square Shopping Center

Are there one-bedroom vacation rentals in Middletown?
You'll find five one-bedroom properties in Middletown to pick from. A one-bedroom vacation rental is a superb choice if it's just two of you or if you're vacationing solo. Toss in more privacy, space and convenience compared to a standard hotel, and you'll be sure to have an unforgettable getaway.
Can I find two-bedroom vacation rentals in Middletown?
Middletown has three two-bedroom vacation rentals for you to pick from. Discover a vacation home with all the comfort and privacy you need at an attractive price on Vrbo.
Are there vacation rentals with WiFi in Middletown?
Middletown has five vacation rentals with WiFi, so you can stay connected while you're on vacation. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming Hollywood blockbusters to checking emails, these Vrbo homes make it easy to go online.
How can I find vacation rentals with air conditioning in Middletown?
Decide on your travel dates and then use the filters to locate vacation rentals with air conditioning in Middletown on Vrbo. With 17 air-conditioned properties to choose from here, you can look forward to a cool and comfortable stay.
How old do you have to be to rent a vacation rental in Middletown?
We advise checking with the Middletown vacation home you want on Vrbo as the age limit differs. However, typically it's 16, 18 or 21.
How long can I rent a vacation rental in Middletown for?
The amount of time you can stay in a Middletown vacation home for is down to the property. Just tap in your travel dates to view available options offering extended stays. They include all you require to make your extended vacation more convenient and enjoyable, such as kitchens and yards. Some Vrbo vacation rentals may also offer weekly or monthly discounted prices, so you can have a longer stay for less.
Does Vrbo offer discounts for vacation homes in Middletown?
Whether you've got your sights set on one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you're sure to find some incredible deals and discounts on Vrbo. From weekend trips to extended vacations, we've got the perfect place for your next Middletown escape.

More Vacation Rentals ideas