House holiday rentals in Middletown

Find and book unique houses on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Middletown house rentals

House rentals with a pool

Guest favourite
Home in Taylorsville
4.91 out of 5 average rating, 23 reviews

Bourbon Trail Lake Home w/ Hot tub & King Bed

SteveRating, 5 starstoday
The place was everything we wanted ton our stay. Sarah was fantastic in responding to any of our questions. I would definitely stay here again!
Top Guest favourite
Home in Mount Washington
5 out of 5 average rating, 45 reviews

Pool*Pickleball Bldg*HotTub*Speakeasy*BourbonTrail

HeatherRating, 5 stars1 week ago
This house was beautiful! Kaeley had everything you could think of (and everything you may have forgotten like coffee or coffee creamer!) the entire premises is an absolute dream, you almost don’t even need to go do anything else because there’s so much to do on property! It was the perfect central spot for some of the farther away things as well like mammoth cave and/or the further away distillery’s! And only 30 mins from Louisville! It was the perfect trip, and the perfect spot and I have no complaints or nothing negative to say about the property!! It was perfect!!
Guest favourite
Home in Shelbyville
4.96 out of 5 average rating, 28 reviews

Pool is Open! + Hot Tub, 10 min to Bulleit

JenniferRating, 5 stars2 days ago
Loved Jill’s place!! It was so beautiful and thoughtfully decorated. Enjoyed our stay there so much!
Guest favourite
Home in Louisville
5 out of 5 average rating, 53 reviews

Countryside Getaway

ZacharyRating, 5 stars6 months ago
We stay here every year when visiting family for thanksgiving. It is perfect for our small family. The host is always so responsive. The property is beautiful. I can’t recommend this airbnb highly enough. Thank you Gordana!!
Top Guest favourite
Home in Bardstown
5 out of 5 average rating, 8 reviews

Farmhouse Luxury! 10 Min to Distilleries! Pool! Ho

KatelinRating, 5 stars2 weeks ago
Our groups stay at the farmhouse was lovely! The surroundings were beautiful, there was plenty of space for everyone, and the separate game room from the house was super convenient! Between the house, game room, fire-pit, and pool/hot tub there is plenty to keep everyone happy and occupied. We had one issue with a shower not draining well and the host responded to my message immediately and sent over a handyman who was very nice and addressed the problem so it worked perfectly for the remainder of our trip.
Top Guest favourite
Home in Prospect
5 out of 5 average rating, 107 reviews

Stay@Peppermint Cottage Norton Commons w/breakfast

BetsieRating, 5 stars1 week ago
Amazing stay. Nicole was super responsive and over the top helpful with info and recommendations. The house was beautiful. Everything exceeded our expectations. Looking forward to coming back !
Top Guest favourite
Home in Prospect
5 out of 5 average rating, 13 reviews

CIRCO 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.
Guest favourite
Home in Taylorsville
4.93 out of 5 average rating, 104 reviews

Ridge Retreat 42 Sleeps 8 + Crib. NEW HOT TUB

GretchenRating, 5 stars2 weeks ago
Suzanne was accommodating, friendly and has a beautiful home. We were lucky to have spent our wedding weekend with her place. Thanks for making it easy.

Weekly house rentals

Guest favourite
Home in Germantown
4.83 out of 5 average rating, 12 reviews

Cozy Cottage House in Louisville-*No cleaning fee*

RonshaRating, 5 stars5 days ago
Nice place and peaceful didn’t want to leave so I stayed two more days. I would come back anytime and will tell friends/family to have great my Airbnb was .
Top Guest favourite
Home in Prospect
5 out of 5 average rating, 62 reviews

Luxury Waterside Retreat|FireTable|WraparoundPorch

SierraRating, 5 stars5 days ago
This was an amazing home to be in for my graduation weekend. My family and I felt right at home. Everything was extremely clean and the hosts were very responsive. The home looks just like the photos and it’s super cozy/homey. This place is great for a family get away and pretty close to everything. I really enjoyed my stay and recommend for all.
Top Guest favourite
Home in Shelbyville
5 out of 5 average rating, 28 reviews

The Back 40

DanRating, 5 stars1 week ago
We had an absolutely amazing stay at this beautiful Airbnb during our bourbon hunting trip in Kentucky. The location couldn’t have been more perfect—less than 30 minutes from both Buffalo Trace and downtown Louisville, which made our bourbon adventures super convenient. The property itself was spotless and incredibly comfortable. One of the highlights was the huge covered deck, which became our sanctuary during a rainy day. We spent hours out there just relaxing, listening to the peaceful sounds of the tranquil creek that flows right in front of the deck. It was like something out of a postcard. Nature lovers will feel right at home here. We saw plenty of deer, hawks soaring above, and even a small herd of cattle that strolled by at nearly the same time each evening—like clockwork! It added such a unique charm to the whole experience. We also made full use of the kitchen and grill, cooking up some delicious local beef while sipping on bourbon in the serene countryside setting. It wa
Guest favourite
Home in Crestwood
4.98 out of 5 average rating, 48 reviews

2King beds+HotTub+FirePit

LorrieRating, 5 stars1 week ago
We wanted a quick, midweek, night away for our 20th Anniversary. We’d had a particularly overwhelming a stressful, busy couple of weeks with other family commitments and a death near the family. We booked the day before our stay- very last minute! Becky & Heather were fantastic hosts. The house was ready, the hot tub looked brand new it was so clean, the backyard is an oasis of relaxation, and everything was just perfect. We were able to relax and enjoy! We ordered take out from the nearby Crestwood Bistro- delicious!! Just wish we’d had more time. We’ll definitely recommend Becky & Heather’s place to friends and family.
Top Guest favourite
Home in Louisville
5 out of 5 average rating, 46 reviews

Convenient & Cozy! Close 2 it all in Louisville!

BlakeRating, 5 stars2 weeks ago
Hands down the best place I have stayed at during by 6 months in the area. Melissa was very responsive and the house was amazing! Will definitely be back again.
Superhost
Home in Jeffersontown
4.79 out of 5 average rating, 39 reviews

Safe, 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 reviews

Country 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 Jeffersonville
4.93 out of 5 average rating, 76 reviews

Beachfront River Cottage

TylerRating, 5 stars3 months ago
This was one of my favorite Air BNB stays to date. The cottage was so incredibly beautiful. It was super well stocked, clean, and there was a great amount of information about the property. We will definitely be back.

Private house rentals

Guest favourite
Home in Louisville
4.95 out of 5 average rating, 41 reviews

Cozy & Chic Home w Backyard | St. Matthews Retreat

JlRating, 5 starstoday
Great location central to everything. within 15-20 min church hill downs. Great place for breakfast is Con Huevos.
Top Guest favourite
Home in Crescent Hill
5 out of 5 average rating, 29 reviews

Little Gem off Frankfort Ave

JonRating, 5 stars1 week ago
Exceptionally clean, quiet, and professional. Thanks!
Superhost
Home in Prospect
5 out of 5 average rating, 3 reviews

Riverfront Cottage

NoahRating, 5 stars2 months ago
This was a cozy getaway with a great view of Ohio river. The decor was spot on. The hosts are wonderful and easy to work with. Gave us the relaxation we greatly needed. Thanks for such a wonderful experience.
Guest favourite
Home in Louisville
4.94 out of 5 average rating, 50 reviews

Historic Woodlawn Park Home

AnnRating, 5 stars5 days ago
Very nice home, great for kids, friendly, flat yard front & back, nice & new kitchen with everything you need to cook. Close to supermarkets, Target, restaurants & shopping.
Guest favourite
Home in Charlestown
4.89 out of 5 average rating, 64 reviews

Entire home: close to downtown.

KimberlyRating, 5 stars1 week ago
We loved that there were dressers for clothing since we stayed a week. It was a very convenient location for where we were working. The neighborhood was nice and it the house felt like home. The couch was comfortable to sit relax on after the work day. It was wonderful that there were food storage containers especially since we cooked in most most meals.
Top Guest favourite
Home in Louisville
4.98 out of 5 average rating, 58 reviews

Home Away From Home w/ full gym, hot tub, & sauna

ShayerRating, 5 stars2 weeks ago
Very clean interior and well taken care of property. Bed is quite comfortable. Appliances and electronics are high end. Amenities are great and had everything you could ask for. Thoughtful touches and complimentary items are highly appreciated. Overall 5 star Airbnb.
Top Guest favourite
Home in Crestwood
4.96 out of 5 average rating, 27 reviews

The Yellow House @ Floydsburg

CarolRating, 5 stars1 week ago
Our stay was fantastic. We selected this location due to our daughter getting married at Duncan Memorial Chapel that was just across the street and was also in close proximity to the reception venue, Shall We Dance. There was plenty of space (bedrooms and baths) for our family and the bridal attendants to stay. The kitchen was absolutely perfect for preparing and serving meals as well as prepping floral arrangements for the wedding and reception. The home provided many areas for people to sit and converse both inside and outside as there are wonderful porches and decks around the home. Scott was a great host and quickly responded to any questions we had prior to our arrival. This was a perfect place to stay as it provided a calming and serene haven from the sometimes frenzied activities that occur during the run-up to a wedding. We're glad we selected this property for our stay.
Top Guest favourite
Home in Mount Washington
5 out of 5 average rating, 26 reviews

The Bourbon Trail Bungalow Ping pong/Foosball/Bar

CydneyRating, 5 stars4 days ago
My sister and I, along with our 3 sons ages 2, 9, and 13 stayed 3 nights while in town for a family reunion and LOVED everything about the house! The kids were thoroughly entertained with all of the activities and it took them no time to make themselves at home. Damon was so accommodating and quick to communicate with any questions we had. The home is beautiful, super clean, well stocked, and comfortable. The home is exactly as it's shown in pictures. The location was perfect for us being 10 minutes from our cousins house and everything else we needed to get to. The neighborhood is very safe and neighbors driving by we're always waving while we enjoyed the front porch. I hope when we come back to visit in the future Damon's home is still up and running so we can stay in a place that truly feels like home!

Quick stats about house rentals in Middletown

  • Total rentals

    40 properties

  • Nightly prices starting at

    $116 NZD before taxes and fees

  • Total number of reviews

    920 reviews

  • Family-friendly rentals

    30 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
  6. House rentals