Middletown holiday lettings

We found 41 holiday rentals — enter your dates for availability

Discover a selection of 16 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

What is the most popular type of holiday rental in Middletown?
In Middletown, holiday houses are the most popular type of rental, with around 12 available throughout the area. These houses typically offer spacious living arrangements, including multiple bedrooms, fully equipped kitchens, and outdoor spaces for relaxation. Many are situated in family-friendly neighbourhoods, providing a homely atmosphere that is ideal for larger groups or families. Additionally, there are several apartments and condos that cater to those seeking a more compact and convenient stay. These often come with modern amenities such as laundry facilities and communal areas, making them suitable for shorter visits.
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?
July is the most popular month to visit Middletown, Kentucky, as it falls within the peak season running from May to July. During this time, visitors can soak up the vibrant atmosphere of the region, which comes alive with various outdoor events and local festivities. The warm summer temperatures, typically reaching the mid-30s Celsius, are great for exploring the charming parks and enjoying leisurely strolls through the town.

For those who prefer a more relaxed experience, the shoulder months of May and June also offer pleasant weather, with comfortable temperatures in the low 20s to mid-30s Celsius, ideal for outdoor activities and sightseeing. This time allows you to appreciate the natural beauty of Middletown while avoiding the height of the summer crowds.

If you're looking for a budget-friendly option, consider planning your visit in December. While this month sees fewer tourists, it provides a unique opportunity to enjoy the festive decorations and local holiday events, creating a charming winter atmosphere that enhances the town's appeal.
Are there any remote work holiday rentals in Middletown?
In Middletown, Kentucky, there are plenty of remote work holiday rentals available, with around 20 options to choose from. These properties are well-equipped to accommodate those looking to work while enjoying a change of scenery. Many rentals feature dedicated workspaces, including desks and comfortable chairs, along with reliable Wi-Fi to ensure a productive environment. Some may even offer additional amenities such as computer monitors and access to a business centre that operates 24 hours. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
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.
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