Middletown vacation rentals

We found 40 vacation rentals — enter your dates for availability

Discover a selection of 17 homes 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.

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Find out more about Middletown

Why visit Middletown

  • Family-friendly attractions: Middletown offers a variety of activities perfect for families, ensuring fun for all ages.
  • Outdoor adventures: Enjoy urban parks and nearby caves, ideal for outdoor enthusiasts and nature lovers.
  • Charming neighborhoods: Explore quaint areas that showcase the welcoming atmosphere of Middletown.
  • Diverse accommodations: Choose from a range of vacation rentals, including cozy homes and luxurious condos.
  • Community warmth: Experience the friendliness of the local community as you discover the region's beauty.

Popular types of accommodation around Middletown

Planning a getaway to Middletown? You're in for a treat. Discover a variety of vacation rentals, including houses, stylish apartments, and luxurious condos. Whether you're searching for a cozy house rental, a scenic view house, or upscale Middletown apartments, we've got you covered. Enjoy the perfect blend of comfort and convenience as you explore all that this charming destination has to offer.

  • Houses: These spacious and fully-equipped homes are the top choice for travelers, offering the comfort and privacy of a home away from home.
  • Apartments: A popular option for those seeking convenience and easy access to local attractions, apartments provide a cozy stay with essential amenities.
  • Condos: Ideal for families or groups, condos combine hotel-like services with the comforts of home, often featuring shared facilities.
  • Cottages: These charming and quaint properties offer a peaceful retreat, perfect for a relaxing getaway.
  • Cabins: Nestled in nature, cabins provide a rustic escape, ideal for outdoor enthusiasts seeking adventure.**

Top attractions in and around Middletown

Middletown, Louisville, Kentucky, is an ideal destination for family vacations, business trips, and outdoor adventures. Visitors can explore a variety of attractions, including urban parks, caves, and historic houses, making it perfect for those seeking a blend of outdoor fun and urban experiences. Whether traveling with family or solo, there’s something for everyone to enjoy in this charming area.

  • E.P. Tom Sawyer State Park: This urban park offers a family-friendly atmosphere with expansive outdoor spaces for hiking, picnicking, and sports. Enjoy the city vibes while immersing yourself in nature just 3 miles from Middletown.
  • Louisville Mega Cavern: An exciting adventure awaits in this vast underground cave, located 10 miles away. Explore zip lines and tram tours in a unique setting, perfect for thrill-seekers and nature enthusiasts.
  • Southeast Christian Church: Situated in Middletown, this church provides a rich cultural experience with community events, inspiring architecture, and a welcoming atmosphere for visitors.

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, and savor the charming atmosphere at Milla Nova Winery. Each destination offers a unique vibe, perfect for creating unforgettable memories together.

Things to do recommended for families

Families visiting Middletown, Louisville can enjoy ice skating at IceLand Sports Complex, embark on an adventure at Danger Run arcade, and experience thrilling kart racing at Bluegrass Indoor Karting, all within a few miles of the area.

Things to do recommended for groups

Explore the vibrant Springhurst Towne Center for shopping and entertainment, enjoy a romantic tour at the Kentucky Artisan Distillery, or hit the greens at Persimmon Ridge Golf Club for a fun outdoor experience. Each destination offers a unique vibe perfect for group travelers.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're traveling with a group, enjoying a family getaway, bringing along your pets, or seeking extended stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Middletown with a group: Think about how many bedrooms you'll require, as well as any additional features like a full kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Middletown with young kids: Traveling with young kids can be quite a challenge. It's important to prioritize their comfort and safety, as well as look for age-appropriate amenities, like a private 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 trip isn’t truly complete without their furry companion. If you can relate to this, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with 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 offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay near Middletown

Exploring Middletown, Louisville, Kentucky, offers a delightful blend of family-friendly attractions and charming neighborhoods. Visitors can enjoy a variety of outdoor activities and relax in the welcoming atmosphere. Nearby, you’ll find vibrant cities and quaint areas perfect for vacation rentals. Whether you seek a romantic getaway or a recreational adventure, Middletown is an ideal base for discovering the warmth of the community and the beauty of the region.

  • Louisville: As the largest city in Kentucky, Louisville is a vibrant hub where culture and entertainment meet. Located conveniently in the heart of the city, Middletown offers easy access to numerous attractions. Visitors flock to Louisville for its diverse experiences, from family-friendly activities to business-themed events. Explore the bustling shopping malls and enjoy live music concerts that reflect the city's rich cultural scene. Don't miss iconic landmarks such as the convention center and stadium, which host a variety of events throughout the year, making it a prime destination for both leisure and business travelers.
  • Woodland Hills: Just 0.7 miles from Middletown, Woodland Hills is a charming village known for its beautiful outdoor spaces and scenic views. This serene area is perfect for families looking to enjoy recreational activities. With access to well-maintained parks and a lovely lake, visitors can indulge in leisurely strolls or invigorating rounds of golf at local courses. The village's inviting atmosphere makes it an ideal spot for those seeking a peaceful retreat while still being close to the vibrant activities of Louisville.
  • Anchorage: Located just 1 mile from Middletown, Anchorage is a quaint neighborhood that combines city amenities with outdoor charm. This family-friendly area offers a variety of shopping options, including shopping centers and malls. Outdoor enthusiasts will appreciate the nearby parks and lake, perfect for picnics and casual walks. Anchorage also features event venues that cater to various functions, making it a convenient base for visitors looking to explore the surrounding attractions while enjoying a suburban atmosphere.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January33.1°F (0.6°C)Light RainMostly CloudyAverageSlightly Low
February36.5°F (2.5°C)Light RainMostly CloudyAverageSlightly Low
March46.2°F (7.9°C)Light RainMostly CloudySlightly HighAverage
April55.6°F (13.1°C)Light RainMostly SunnyAverageSlightly High
May65.7°F (18.7°C)Light RainMostly SunnyAverageSlightly High
June73.9°F (23.3°C)Light RainMostly SunnySlightly HighAverage
July77.2°F (25.1°C)Light RainMostly SunnySlightly HighAverage
August75.6°F (24.2°C)Light RainMostly SunnyAverageAverage
September69.8°F (21.0°C)Light RainMostly SunnyAverageSlightly High
October58.1°F (14.5°C)Light RainMostly SunnySlightly LowAverage
November45.9°F (7.7°C)Light RainMostly SunnySlightly LowAverage
December38.8°F (3.8°C)Light RainMostly CloudySlightly LowSlightly Low

Booking with Vrbo is simple

Are you hoping to cut costs on your upcoming trip? Being flexible with your travel dates can help, as prices tend to vary. Additionally, opting for an extended stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of 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 receive OneKeyCash on your entire booking. Being the planner truly pays off. When you join our travel rewards program, One Key, you’ll gain access to exclusive member discounts and earn OneKeyCash on eligible rentals. Sign up today and begin enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, or easily view and organize your travel plans. You can find all the properties you've saved and booked categorized under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Middletown?
In Middletown, vacation houses are the most popular type of rental accommodation, with about 12 available throughout the area. These homes typically offer spacious layouts, multiple bedrooms, and amenities like fully equipped kitchens and private outdoor spaces, making them suitable for families or groups. Additionally, there are several apartments and condos available, providing a range of options for travelers looking for comfortable stays.
How much does it cost to rent a vacation home in Middletown?
Prices for vacation rentals in Middletown vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Middletown to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Middletown vacation house rentals?
You can find great discounts on house rentals in Middletown on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What are popular rental amenities in Middletown?
In Middletown, popular vacation rental amenities cater to a variety of traveler needs, ensuring a comfortable stay. Most rentals feature fully equipped kitchens, allowing guests to prepare meals at their convenience. Many properties also include outdoor spaces such as decks or patios, superb for enjoying the pleasant Kentucky weather. Onsite parking is a standard amenity, making it easy for guests to explore the surrounding area without hassle. Additional conveniences like blenders for smoothies or cocktails and designated office spaces for those needing to work remotely further enhance the experience.
Can I find family house rentals in Middletown?
In Middletown, Kentucky, there are several family-friendly house rentals available, offering a variety of accommodations for groups. Many of these homes feature spacious living areas, fully equipped kitchens for preparing meals, and comfortable bedrooms to ensure a relaxing stay. Outdoor spaces, such as patios or yards, provide a great spot for children to play and families to gather.

This charming suburb is conveniently located near attractions like the Oxmoor Center for shopping and dining, as well as the nearby parks that offer recreational amenities. Visitors can easily explore the local community, which boasts a friendly setting and plenty of opportunities for outdoor activities.
Can I rent a vacation home with a pool or hot tub in Middletown?
In Middletown, Kentucky, there are several vacation homes available for rent that feature pools and hot tubs. This charming suburb of Louisville offers a variety of rental options, including spacious family homes and cozy retreats. Travelers can expect amenities such as private swimming pools, relaxing hot tubs, outdoor seating areas for enjoying the sunshine, and fully equipped kitchens for convenient meal preparation. Some properties may also include backyard spaces ideal for barbecues and family gatherings, making them superb for both relaxation and entertaining.
Are there any Middletown vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Middletown with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I book pet-friendly vacation rentals in Middletown?
Yes, you can book pet-friendly vacation rentals in Middletown, Kentucky. The area offers a selection of around 11 vacation rentals that welcome pets, providing a comfortable stay for travelers with furry companions. Many of these properties come equipped with amenities such as spacious backyards, fully furnished kitchens, and cozy living areas, making them ideal for both relaxation and entertaining.

Middletown is known for its friendly suburban atmosphere, with easy access to nearby parks and recreational spaces where pets can enjoy outdoor activities. Local attractions, shopping centers, and dining options are also conveniently located, ensuring that both you and your pet have a pleasant and enjoyable stay.
Can I find long-stay vacation rentals in Middletown?
A long-stay vacation rental in Middletown is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Middletown for a vacation rental?
The best time to visit Middletown for a vacation rental is during the peak season from May to July, with July being particularly popular among travelers. This vibrant time of year attracts families and adventure-seekers looking to enjoy warm temperatures and a variety of outdoor activities. Visitors can explore local parks, engage in recreational sports, and experience the lively community events that happen throughout the summer.

In July, you can expect pleasant weather, typically ranging from the mid-70s to the low 90s Fahrenheit, great for enjoying outdoor activities. Whether you're picnicking in the parks or strolling through the charming downtown area, the atmosphere is buzzing with energy and excitement.

If you're considering a more budget-friendly option, December presents an excellent opportunity to visit Middletown. While it's a quieter time of year, it offers a unique charm, especially with festive holiday decorations that create a cozy atmosphere. You can enjoy a slower pace and experience the local culture in a more intimate setting.

Ultimately, the best time to visit Middletown depends on your preferences. If you thrive on vibrant summer activities and community events, aim for the peak months.
Are there any remote work vacation rentals in Middletown?
In Middletown, Kentucky, there are several remote work vacation rentals available, with around 21 options to choose from. These rentals cater specifically to those looking to combine work and leisure. Many properties come equipped with essential amenities such as high-speed internet, comfortable laptop workspaces, and free Wi-Fi in public areas, ensuring a productive environment.

Travelers can expect a variety of accommodations, from cozy apartments to spacious homes, often featuring comfortable living areas where one can unwind after a workday. Additionally, some rentals may include kitchens for preparing meals, making it convenient for longer stays. The welcoming atmosphere of Middletown, with its local parks and community amenities, adds to the appeal for remote workers looking for an engaging yet tranquil setting. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Middletown vacation rental?
Book your Middletown vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Middletown, Kentucky, United States of America?
In Middletown, Kentucky, visitors can explore several attractions that highlight the charm of the area. One of the main draws is the Middletown Commons, a shopping center featuring a variety of retail stores and dining options, great for those looking to enjoy a day of shopping and good food. The nearby Skyview Park offers outdoor recreation opportunities, including walking trails, playgrounds, and sports fields, making it a great spot for families and outdoor enthusiasts.

Additionally, the historic Middletown area showcases beautiful architecture and the welcoming community vibe, which can often be experienced during local events and festivals held throughout the year.
Can I change or cancel my Middletown home rental booking on Vrbo?
To find Middletown vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Middletown vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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