Discover a selection of 366 vacation rentals in Middletown, KY that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and kitchens. Prices start at $114 per night, and houses and condos are popular options for a stay in Middletown. Either way, you'll find a rental for everyone's needs.
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Destination guide

The lively area of Middletown awaits your stay

Enjoy the live music and other features of Middletown. Renowned for its cafés, baseball games and chocolate shops, this city welcomes all visitors. Muhammad Ali Center and Churchill Downs are just a couple of the must-sees in the area. With a vacation rental, you get a home away from home—many rentals offer full kitchens and outdoor grills for some home cooking.

Activities

Sightseeing in and around Middletown

Are you looking for top things to see and do during your stay? Venture out of your vacation home and check out everything that makes Middletown a one-of-a-kind vacation spot. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Long Run Golf Course (5.9 mi / 9.5 km)
  • Louisville Mega Cavern (9.7 mi / 15.7 km)
  • Louisville Zoo (9.9 mi / 15.9 km)
  • Kentucky Kingdom (11.9 mi / 19.2 km)
  • Eagle Creek Golf Course (13.1 mi / 21.1 km)
  • Talon Winery (14.6 mi / 23.5 km)
Natural features

Exploring the natural landscape of Middletown

Whether you're looking for adventure or just want to spend some time taking in the scenery, Middletown is a great spot to appreciate mother nature. These are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city center:

  • E P Tom Sawyer State Park (2.9 mi / 4.6 km)
  • Skyview Park (3.3 mi / 5.4 km)
  • Beckley Creek Park (3.8 mi / 6.2 km)
  • Yew Dell Botanical Gardens (7.2 mi / 11.6 km)
  • Seneca Park (7.6 mi / 12.2 km)
  • Kennedy Park (8.8 mi / 14.2 km)
How to get there

How to get to and around Middletown

The nearest airport is in Louisville, KY (LOU-Bowman Field), located 7.4 mi (11.9 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to Louisville, KY (SDF-Louisville Intl.), which is 12.1 mi (19.4 km) away.

How many vacation rentals are available around Middletown, KY?

Our 2020 property listings offer a large selection of 366 vacation rentals around Middletown. From 264 house rentals to 43 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What is the best area to stay when traveling to Middletown?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Middletown:

  • Old Louisville: 121 vacation rentals
  • Cherokee Triangle: 135 vacation rentals
  • Deer Park: 83 vacation rentals
  • Tyler Park: 115 vacation rentals
  • Crescent Hill: 54 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular point of interests near where I can stay when traveling to Middletown?

Vrbo offers a large selection of vacation rentals near lovely places in Middletown. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Eastgate Shopping Center: 733 vacation rentals
  • Village Square Shopping Center: 729 vacation rentals
  • Churchill Downs: 716 vacation rentals
  • Taylorsville Lake State Park: 83 vacation rentals
  • Charlestown State Park: 701 vacation rentals

But there are many other points of interest around Middletown listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Middletown?

Yes, of course. Vrbo has 264 Houses in Middletown. Our other popular types of vacation rentals in Middletown include:

  • Condos/Apartments: 43 rentals available
  • Cabins: 3 rentals available
  • Cottages: 3 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Bungalows and more.

Can I find a vacation rental with pool in Middletown?

Yes, you can select your preferred vacation rental with pool among our 38 vacation rentals with pool available in Middletown. Please use our search bar to access the selection of vacation rentals available.

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