Holiday rentals in Middletown

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Popular amenities for Middletown holiday rentals

Stay near Middletown's top sights

Havana Rumba Middletown32 locals recommend
Main Event Louisville31 locals recommend
Mark's Feed Store29 locals recommend
The Village Anchor24 locals recommend
Xscape Theater Blankenbaker 1422 locals recommend
The Fresh Market13 locals recommend

Other great holiday rentals in Middletown

Superhost
Holiday home in Louisville
4.77 out of 5 average rating, 30 reviews

Historical Mansion 7BD Vacation Home in Derby City

WaqasRating, 5 stars5 months ago
Beena's home was excellent for our large group passing through. It's a very unique property with each room in a different theme, and an incredible outdoor grounds which really makes it feel special. we had a great stay and would love to go back!
Top guest favourite
Home in Shelbyville
5 out of 5 average rating, 22 reviews

Bourbon by the Lake

MohamedRating, 5 stars3 months ago
Emily's home was very clean with beautiful views. It is a perfect seasonal getaway, with clean beds/linens, great bathrooms/showers, and a fully stocked kitchen. We particularly liked the outdoor firepit. I would definitely consider Emily's place again in the future.
Top guest favourite
Home in Elizabeth
4.98 out of 5 average rating, 126 reviews

Cabin on Lake Close to Louisville Ky

BeckyRating, 5 stars2 days ago
Great place to stay! We went for a girls trip and wanted something a little secluded but not too far from the city and the location was perfect. The house looked just like the photos and was very clean.
Guest favourite
Flat in Central Business District
4.99 out of 5 average rating, 88 reviews

Sleek Luxury Apt: King Bed, Coffee Bar & Pool!

ShelleyRating, 5 stars2 weeks ago
This apartment was in a perfect location, super clean, and when I had an issue with the key fob box (user error), the owner was very quick to respond and help!
Guest favourite
Flat in Louisville
4.83 out of 5 average rating, 121 reviews

Highlands Harmony House - Near Cherokee Park

TinaRating, 5 stars3 weeks ago
We loved the old, historic neighborhood and walked around this and other nearby neighborhoods often. The house is right next to Cave Hill Cemetery and probably only a couple blocks from Mohammad Ali's grave. The host is very nice. The studio is clean and the bed is comfortable. It does not have a kitchen table but has a few smaller TV table-type tables for which to eat. We wanted to host my wife's daughter for movie and pizza but the studio was not really amenable to hosting a guest; however, it was fine for the two of us. The screened porch looks nice but the weather was cold, so we did not use it. The kitchen is small but adequate. We could always park within a block of the house, but the street was relatively narrow and was a dead-end, so it was difficult to maneuver. If you are uncomfortable parallel parking, it could be a problem for you.
Guest favourite
Farm stay in Simpsonville
4.9 out of 5 average rating, 62 reviews

Spacious Home with Beautiful Views

CourtneyRating, 5 stars3 weeks ago
We enjoyed our stay! We would recommend the house to everyone, it was beautiful, private, spacious, clean, and just what we needed!
Guest favourite
Apartment in Highlands
4.94 out of 5 average rating, 189 reviews

Large Townhouse, Walk to All! King beds, 2.5 baths

AveriRating, 5 stars2 days ago
Super clean, spacious condo- perfect for our group of 4! We came into town for the St. Patrick’s Day parade and Dierdre’s place was the PERFECT location- included a parking spot and we were able to walk to various restaurants, bars, etc. Flexible check in process and very responsive to messages! Would definitely stay here again!
Top guest favourite
Home in Louisville
5 out of 5 average rating, 16 reviews

Bourbon Country Cottage

NatalieRating, 5 stars3 weeks ago
We couldn’t have asked for better accommodations! Clean, comfortable, and very nice. We loved all the “extras” that went with the home. We will definitely recommend this home to anyone. Thank you, Julie, for making our stay in Louisville so wonderful. Natalie F. February 2025

Quick stats about holiday rentals in Middletown

  • Total rentals

    50 properties

  • Nightly prices starting at

    £54 before taxes and fees

  • Total number of reviews

    1.1K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Kentucky
  4. Jefferson County
  5. Middletown