Middletown holiday lettings

We found 40 holiday rentals — enter your dates for availability

Discover a selection of 17 homes and other holiday rentals in Middletown that are perfect for your trip. Holiday homes provide the best amenities for your family, friends or furry companion, such as Wi-Fi and parking. Whatever you're looking for, you'll find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

How much does it cost to rent a holiday home in Middletown?
Prices for holiday 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 holiday 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.
Are there any Middletown holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Middletown with parking available—perfect for families or travellers 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 find long-stay holiday rentals in Middletown?
A long-stay holiday rental in Middletown is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Middletown for a holiday rental?
The peak season for visiting Middletown, Kentucky, spans from May to July, with July being the most popular month. This vibrant period attracts a diverse range of travellers looking to enjoy the warm summer weather and the local festivities. With temperatures typically ranging from 20 to 30 degrees Celsius, it's an ideal time for outdoor activities, such as exploring the nearby parks, enjoying picnics, or strolling through the charming downtown area.

In addition to the pleasant climate, visitors during this time can partake in local events and community gatherings, making for a lively and engaging holiday atmosphere. Families, couples, and adventure seekers alike will find plenty of opportunities to create memorable experiences.

For those seeking a more budget-friendly option, consider planning your visit in December. During this time, this month offers a unique charm, especially with festive decorations and local holiday events that can provide a delightful experience without the crowds.
How early should I book a Middletown holiday rental?
Book your Middletown holiday 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 holiday 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 enjoy a variety of attractions that showcase the charm of this suburban community. The Middletown Commons offers a selection of shops and eateries, making it a great spot for local dining and shopping experiences. Additionally, the nearby Skyview Park features walking trails, playgrounds, and sports facilities, great for family outings or leisurely strolls.

For those interested in history, the area is close to the historic town of Shelbyville, where one can explore the Kentucky Museum of Art and Craft, highlighting local artisans. The proximity to Louisville also provides easy access to attractions such as the Kentucky Derby Museum and the Louisville Mega Cavern for those willing to venture a bit further.
Can I change or cancel my Middletown home rental booking on Vrbo?
To find Middletown holiday 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 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 travellers 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 cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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.

More holiday ideas