Family-friendly vacation rentals in Middletown

Great location. Easy check in and out.

This is a wonderful place to stay if you are visiting UConn or the surrounding area. Keri and Jason were fabulous hosts and very responsive to my needs. Keri even anticipated needs by offering to have a fresh cup of coffee ready for me on the AM. Everything was perfect for my stay and there was definitely a comfortable feel. I will definitely be staying here in the future.

Jeannine’s home was an absolute gem! We had our annual girls weekend here and felt right at home. The house was so cozy and warm yet had ample space for me and the girls to sit and chat together. We loved that the house was lived in with family photos and mementos around, rather than being sterile like many other bnbs we’ve stayed in. There was also so much to do in the surrounding area! I would definitely recommend this stay :)

We came as a group of friends with a baby to stay at Blake and Tracy's house, and we had a great stay. They were very communicative and accommodated all our requests to ensure our stay was excellent. They asked in advance if it would be okay for their child to stay in his room inside the house, and we agreed. We didn’t see him at all during our stay, and it didn’t disturb us in the slightest. The fact that Blake and Tracy live right next door was convenient, as they were readily available for anything we needed, but we never felt their presence. We will definitely come back!

My husband and I stayed with our 19-month-old son for three nights and it was a perfect choice! Susan had a toys and books that he loved, as well as a sandbox and pool outside - and the home was stocked with everything we needed for our stay. We used the location as a jumping off point for other activities and then had quiet afternoons at the house while my husband rode his bike (we saw lots of other cyclists!). If you are vegan or vegetarian, check out the Shoreline Diner in Guilford - it was delicious.

It was great. Everything was the complete opposite of what I expected

This is at least our 4th time staying at what we call "The Farm" and it is our favorite getaway! We even got my brother to drive 1.5 hours out of his way on his family trip to Boston so he could check it out. A rare gem!

Cannot thank Stephen enough for taking care of us after a major mess up. We were able to get in and relax and enjoy. So grateful for all he did for us on a graduation weekend.

Noel was an incredibly gracious and friendly host, providing us with everything we needed for a great stay in her apartment. The apartment itself is so cozy; we particularly enjoyed the library room and exploring the hundreds of titles Noel keeps there. I would recommend Noel’s apartment to anyone that is making a trip to New Haven.

Was the perfect little get away for us. And it was nice to find a place that accommodated the dogs so well. We appreciated being able to get to places easily but at the same time have a peaceful place to return to.

Loved the tasteful decor, and the way this historic home has been modernized yet still holding its victorian charm. Many nice touches, and everything was nicely arranged. The bedroom is spacious and lovely. My daughter and I thoroughly enjoyed our time together staying at Lizzy's place.

This was the perfect place for our family to stay! There was plenty of space and everything we needed was provided. We would definitely stay here again!

I really enjoyed my stay here. The place was eclectic and comfortable. I loved how open and spacious the home was and appreciated the peacefulness of the area. I would definitely stay here again on future visits.

Very nice place and location is amazing. We were grateful that our host provide some basic amenities - coffee, shampoo and condtuoner, etc. Made our visit easy and very pleasant. Thank you!

I chose Marlene’s lovely spot primarily because it was in a location convenient for short trips to visit family and friends in Wallingford, Middlebury and Middletown while on my way south from New Hampshire. The peaceful, quiet surroundings along with a spotless, well-appointed accommodation made it very appealing: highly recommended.

Thank you for a wonderful stay and accommodating an extra night.

House was very easy to get to and very clean. Surrounding neighborhood was nice and quiet. Outside igloo was warm and cozy. Downstairs game room was a hit with the big kids.

This was our second time back to the pool house and it was amazing, again. We thinks of everything to make you feel welcome. Milk and eggs in the fridge. Muffins and croissants waiting for you. Pristine home. Fully stocked kitchen. I was even able to host a few family members for Christmas dinner and had everything I needed to make a lovely dinner. We also travel with two dogs and Sue is so accommodating, making our pups feel right at home. Thank you, Sue, for making our holidays away from home so peaceful and enjoyable.

We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!

Felt right at home, check in was very easy, beautiful place, very friendly enjoyed his place thinking to coming back again my business send me to Connecticut! Thank you!

We enjoyed the coziness of the pool house during our Thanksgiving stay. The location was close to our family and friends. It was private and quiet. Alice responded promptly to our questions. We would like to return when the weather is warmer to take advantage of the pool and the outside surroundings. The Goulds

We had a lovely stay at Eric's home. The home exceeded our expectations and we felt right at home. The decor was warm and inviting. Everything you could possibly need was in the stunning, modern kitchen. The beds were all comfortable and we slept very well. The property was very peaceful. We enjoyed seeing deer, turkeys and hawks each day. The fixtures in the home were modern, clean and high-end. It was great being so close to Greenport with it's wonderful restaurants and shops. We can't wait to return.

This wonderful antique home is in a Beautiful spot in the heart of Litchfield CT, and a delight early spring when the fields of daffodils awake! This unique 1793 house has a great view & sunset, fireplace, simple spa/gym making it a gem even when the pool is closed. Nearby the town with lots to offer and local farms for food shopping too. What’s not to love 💛 Bonus is a great host offering a home that is in touch with the realities of rentals, pets and people -not picky, precious or punitive. Happy to recommend and return! Thank you Elizabeth!

The location was great and a nice place to walk. Lots of stuff to see and do that’s not far away. We would come again.