Family-friendly vacation rentals in Middletown

Beautiful lake house with perfect amenities! I would definitely recommend!

This cabin was the perfect place for our family to celebrate the holidays together. The Christmas tree and decorations really added to our enjoyment. Keith and Leslie have taken the extra step to ensure a comfortable and relaxing stay. We were especially impressed at how well stocked the kitchen is. Keith and Leslie are such wonderful and accommodating hosts. We look forward to returning again (perhaps when the weather is warmer, I would really have enjoyed having coffee on the front porch or watching the sun set before bedtime)!

This house was perfect for our family (8 adults). Julie was very responsive, even when we locked ourselves out of the house late on night. Nice neighborhood too!

The hosts were always available and helpful if we needed anything. The location was easy to get to, was in walking distance to Z Bar (Zanzabar) when the fun ones wanted to go out after the old folks went to bed, and had all the eminities needed (except a crock pot). There were 10 people in our group and we had a wonderful early Christmas. It was a great spot to meet between Wisconsin and Alabama. This house is amazing bc it is old, huge, and very well-updated! We would all stay here again!!

One of the best Airbnb’s I’ve stayed in! Lots of extra little amenities, the decor was unique and well thought out, and the location was perfect. We travel to the area often and would definitely book again.

very clean and spacious home. Enjoyed the large table for family game night. only possible downside is the lack of cable TV provided but roku tv for streaming services. We really enjoyed our time and would love to return!

Great place

Very spacious home in a good location. 20 minute drive to downtown and many restaurants and shopping located only a few minutes away.

Local traveler, needed a place to call home for the weekend while my home was up for sale and being shown. Nice location, lots of room to stretch out, tasteful decor, and very well stocked kitchen.

This house is so unique and full of character. We loved the charm, the theme in every room, just everything. Enough room to gather and hang out, but also spaced out enough to have all the privacy you need. Kim is a great host and we will gladly stay at the Guesthouse again!

Beautiful home, so full of history and charm. We very much enjoyed our stay. It was a bit chilly at night but the host was responsive and helpful. Would love to stay here again!

great place in a quiet neighborhood, good option if you are looking somewhere near Ford stamping plant

Ross is an amazing host. Among the best! He is very kind, proactive, and responsive in communication. The house is set up beautifully for guests. It's hard to describe, but just little things everywhere--signs for guests so they know what around the house and what they can use, a chalkboard for a shower schedule, games, book, work out equipment. Plenty of towels, pillows, etc. It was like everywhere we turned we were like "hey, look at that." It was really warm and fun place to stay. Thanks Ross! Your hospitality made for a wonderful stay!

Second year here, we will be back!! Thank Daniel

Me and a couple of friends had a spontaneous weekend trip for my boyfriend’s birthday. Everything about our stay was perfect, especially Alexandria’s home! We went on bourbon tours, to the museum and dined at local restaurants, all within good range of her home. We can’t wait to come back! I’d definitely recommend to anyone looking for a beautifully designed cozy home in the heart of Louisville.

I had the pleasure of staying at this charming townhouse for my graduation, and it was the perfect choice. The home is warm and cozy, with a welcoming atmosphere that made me feel right at home. Located in a quiet, peaceful little town, it offered the perfect escape for a few days of relaxation after the hustle and bustle of graduation. The townhouse itself has so much character and charm, blending vintage appeal with modern comfort. One of my favorite features was the "Paying It Forward" cabinet—it was such a thoughtful touch! The idea of leaving or taking items for others really made the stay feel even more special. Overall, it was a lovely retreat, and I truly enjoyed my time there. Highly recommend it for anyone looking for a peaceful getaway with a homely feel.

Our family of 4 were extremely comfortable in this wonderful, convenient location. Easy check in, great amenities. The pool area was a ton of fun and our kids had a great time. We met Keegan briefly and he was kind and welcoming. Definitely recommend and will try to stay again if we are in town.

It was perfect for our family and was close to the family that we travelled to visit!

Our family of 6 stayed between Christmas and New Years. Like Alicia and Glenn, we also homeschool our four kids (ages 12-6). We were worn down from the holidays and daily life, so were looking for a refreshing time away from home. Our stay was exactly that. The home and property were extremely peaceful being out in the woods. We did several trail walks and explored the creeks around the property. The kids thought the circular nature of the home, and hot tub were fun too. I appreciated the various Christian decor in the home, it gave me some things to think about as we hung out. But even more than all of that, we had a wonderful chat with Alicia and Glenn that was very refreshing to our spirits. If you are looking for a peaceful, quiet getaway that is focused on Jesus and the holy spirt this is the place for you. Make sure you read all the description in the listing so you know what you are renting. If you do that, you'll be very pleased :) In Christ, Dave & Maura

Our family visited Alecia’s place close to Christmas and she was so thoughtful to have a Christmas tree set up for us upon our arrival. We thoroughly enjoyed our stay!! I would definitely recommend to anyone that would appreciate a quiet spacious setting!

Ramona and Steve were fantastic hosts. They made us feel right at home. Their location is beautiful and peaceful and just good for the soul! If my family and I are ever in the area again we will definitely love to visit again!

If you are looking for a tranquil, clean spot to decompress and get away from the rush rush that life is, look no further. Such a relaxing place to stay that felt like home. We loved listening to the waterfall feature and watching the birds play and just enjoying nature❤️

Couldn’t ask for a better place to stay in Louisville. The property had EVERYTHING we needed, close to the highway and literally everything FUN and kid friendly, groceries, parks, restaurants, shopping and access to the cutest, trendy neighborhoods! Amy and her family were amazing hosts. The house was clean and stocked for our long stay with towels, dishes, pots/pans, coffee - we needed nothing! We had the best time, felt safe, and will most likely rent this property again!

We’ve stayed here several times over the last few years and we plan on continuing to do so on our annual Kentucky trip.