
Holiday rentals in Middletown
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Top-rated holiday rentals in Middletown
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in Middletown

Flat in Louisville
4.86 out of 5 average rating, 7 reviewsExpansive 1-Bedroom Suite | Pool, Parking & Gym
TaraRating, 5 stars3 months ago
Comfortable and spacious apartment. Had everything I needed and host was very helpful and responsive.
Top guest favourite

Cabin in New Pekin
4.93 out of 5 average rating, 61 reviewsAnjuna House - a Scandi riverfront forest getaway
TarekRating, 5 stars2 days ago
This place is immaculate. One of the best Airbnb's we have ever stayed in. The design of the home is beautiful and truly feels like your in nature. Top notch in every respect. Couldn't believe it was just nestled in the woods. Fire pit and outdoor shower were amazing amenities. Theater in basement was a nice touch as I got the watch the Pacers play Game 1 of the NBA Finals! Bed were comfortable and the entire home was spotless. The bathrooms may be some of the nicest parts of the home. Every attention to detail was made here and it shows.
Superhost

Home in Jeffersontown
4.79 out of 5 average rating, 39 reviewsSafe, comfortable, & convenient!
JeremyRating, 5 stars2 weeks ago
My Family and I 7 of us loved the location. Minutes from shopping, interstate, food, large enough yard to enjoy catch or just sitting together. Everything was clean and as described. The only thing I personally would focus on a bit more is yard maintenance, there wasn't anything crazy just some cleanup and trimming. Rob was a great host overall and had I needed anything I'm sure he would have gladly assisted however he could. I will book here again the next time I'm in the Louisville area!
Top guest favourite

Home in Finchville
5 out of 5 average rating, 38 reviewsCountry Retreat on Bourbon Trail - Fire Pit - King
LaceyRating, 5 stars1 week ago
I honestly had an amazing experience staying here. From the moment I arrived, everything was just perfect. The place was exactly as described—clean, cozy, and beautifully maintained. You can tell the host really cares about the details, from the thoughtful touches around the space to how easy they made check-in and communication. The location was fantastic, and it felt like a home away from home. Whether I was relaxing after a long day or exploring the area, I always looked forward to coming back to this space. The host was incredibly welcoming, kind, and responsive—truly one of the best I’ve encountered on Airbnb. They went above and beyond to make sure my stay was comfortable. I would absolutely stay here again and highly recommend it to anyone looking for a top-tier Airbnb experience. Thank you so much for the amazing hospitality!
Top guest favourite

Home in Prospect
5 out of 5 average rating, 13 reviewsCIRCO LOCO - uNCommon Stay
MattRating, 5 stars2 months ago
This was a very fun and unique place to stay. The decorating and attention to detail was great. Comfortable bed and furniture. Norton Commons is a cool neighborhood with lots to do and great restaurants. It was a memorable place to stay.
Top guest favourite

Home in Louisville
4.98 out of 5 average rating, 108 reviewsCharming Bungalow on 1.5 Acres in Amazing Location
JacobRating, 5 stars5 months ago
Fantastic stay at Hummingbird for Christmas - great host and very well thought out home.
Guest favourite

Guest suite in Louisville
4.84 out of 5 average rating, 58 reviewsSpacious one bedroom first floor suite
NessaRating, 5 stars2 weeks ago
Amazing experience, clean, private, beautiful surroundings and backyard. Hot tub and sauna were a great bonus and Selam was a very pleasant host. I highly recommend, 10/10 and the price was reasonable and worth every penny.
Top guest favourite

Guest house in Louisville
5 out of 5 average rating, 57 reviewsBreakfast At Tiffany's
RobRating, 5 stars5 days ago
I stayed here for a week on a business trip and it was absolutely perfect. really easy to get to, nice quiet neighborhood and perfectly placed to get around the city and surrounding areas. I highly recommend checking out some of the trails and parks on the Louisville loop 😊 I feel like the place actually felt bigger than it looked in the pictures, it was lovely and clean, comfy bed and shower was hot with good water pressure. Tiffany and her husband (so sorry I forgot your name 😭) were great hosts. really responsive to queries and super friendly, but also kept to themselves when I didn't need them so it you prefer privacy then you will also be happy here. If I'm back in town again I will definitely stay here again and highly recommend to anyone who is considering it.
Quick stats about holiday rentals in Middletown
Total rentals
50 properties
Nightly prices starting at
₹5,982 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
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- Buffalo Trace Distillery
- Big Four Bridge
- Kentucky Kingdom & Hurricane Bay
- Louisville Slugger Field
- Louisville Slugger Museum & Factory
- Kentucky Derby Museum
- Anderson Dean Community Park
- Muhammad Ali Center
- Valhalla Golf Club
- Heritage Hill Golf Club
- Charlestown State Park
- Waterfront Park
- Angel's Envy Distillery
- River Run Family Water Park
- Kentucky Science Center
- Evan Williams Bourbon Experience
- Falls of the Ohio State Park
- Big Spring Country Club
- Frazier History Museum
- Turtle Run Winery