Middletown vacation rentals

We found 42 vacation rentals — enter your dates for availability

Discover a selection of 16 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, with about 12 available in the area. These properties typically feature multiple bedrooms, fully equipped kitchens, and spacious living areas, making them suitable for families or groups. Additionally, there are several apartments and condos scattered throughout the neighborhood, offering travelers a more compact and convenient option. These apartments and condos generally include essential amenities such as kitchen facilities and comfortable living spaces, providing a homely atmosphere for guests.
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 include fully equipped kitchens, which are essential for travelers who prefer to cook their own meals. Many rentals also feature blenders and coffee or tea makers, allowing guests to enjoy homemade beverages during their stay. Decks or patios are common as well, providing outdoor spaces for relaxation and socializing. Additionally, some rentals are pet-friendly, suiting those who wish to bring their furry companions along on their travels.
Are there any family house rentals in Middletown?
In Middletown, Kentucky, there are several family-friendly house rentals available, providing ample options for those traveling with children. This charming suburb has a variety of spacious properties that often feature amenities such as fully equipped kitchens, cozy living rooms, and outdoor spaces for kids to play. Travelers will appreciate the comfort and convenience these homes offer, allowing for quality family time and the ability to prepare meals together.

The locale is also close to several parks and recreational areas, great for outdoor activities. Nearby attractions include the lovely E.P. "Tom" Sawyer State Park, which offers trails, playgrounds, and picnic spots. Additionally, families can explore local dining options and shops that reflect the friendly, community-oriented vibe of Middletown.
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 suburban area offers a comfortable retreat with easy access to the amenities of nearby Louisville. Travelers can expect properties with inviting outdoor spaces, including private pools and hot tubs, superb for relaxation after a day of exploring. Many rentals also come equipped with full kitchens, spacious living areas, and outdoor dining options, making them ideal for families or groups.
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.
Are there pet-friendly vacation rentals in Middletown?
In Middletown, Kentucky, travelers can find a variety of pet-friendly vacation rentals, with around 13 options available. The area features homes equipped with essential amenities such as fully stocked kitchens, comfortable living spaces, and often outdoor areas where pets can enjoy the fresh air. Many of these rentals are conveniently located near local parks, making it easy for guests to take their pets for walks or playtime.

Nearby, residents and visitors can explore the beautiful parks and green spaces, which provide ample opportunities for outdoor activities with pets. The community atmosphere and access to pet-friendly locations enhance the overall experience for those traveling with furry companions.
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?
July is the most popular time to visit Middletown, Kentucky, as this month falls within the peak season that spans from May to July. During this period, travelers flock to the area for summer festivities, local events, and outdoor activities that take advantage of the warm, inviting weather. With temperatures typically ranging from the mid-70s to low 90s Fahrenheit, July offers ideal conditions for enjoying parks, exploring nearby attractions, and participating in community celebrations.

For those considering a more budget-friendly option, December presents a wonderful opportunity to enjoy Middletown's cozy charm without the crowds. The holiday season brings a festive atmosphere, where you can partake in local events and enjoy seasonal decorations, all while taking advantage of lower rental rates.

Ultimately, your experience in Middletown can vary greatly depending on whether you prefer the vibrant energy of peak summer months or the peaceful, festive spirit of winter.
Are there any remote work vacation rentals in Middletown?
In Middletown, Kentucky, there are numerous options for remote work vacation rentals, with around 21 available throughout the area. These rentals cater specifically to those who need a productive environment, featuring amenities such as dedicated office spaces, high-speed Wi-Fi, and comfortable desks equipped with ergonomic chairs. Many properties also offer additional features like 24-hour access to business centers, computer monitors, and laptop workspaces to support your work needs.

The town itself is conveniently located near various points of interest, including parks and local shops, providing a great balance between work and leisure. 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?
In Middletown, Kentucky, visitors can explore various attractions that reflect the area's charm and history. The city features beautiful parks such as the Middletown City Park, which offers walking trails, playgrounds, and picnic areas, ideal for family outings. The nearby Oxmoor Center is a popular shopping destination, providing a variety of retail options and dining experiences.

For those interested in local history, the nearby Hurstbourne Parkway showcases a blend of residential and commercial areas, with historical sites and modern amenities.
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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