Family-friendly holiday rentals in Middletown

My family enjoyed their short stay at Camilla’s apartment. The apartment was a beautiful place.

Our stay was peaceful located in a great place , the home its self was perfect if we come back next year we will book this place again

We have been staying here over the last 4 years, when we visit UConn, and will miss it now that our daughter has graduated. Keri is wonderful host, welcoming & accommodating. Her home in the woods is a refuge, comfortable, peaceful, and minutes from campus.

Amazing! We really enjoyed our stay. Abby and David are extremely hospitable, responsive, and friendly hosts. The house is beautiful, clean, and well-located. The pool, hot tub, desk, and back garden are even larger and more beautiful in real life. We will definitely be back. Thank you Abby and David!

This spot was a great find. Hadn't been to Shelter Island before. I found the location super convenient. Literally every place I went was 5 mins on GPS from her house. She was very clear about everything, responsive to emails, and everything was as described, however the pictures don't do it justice. Beautiful home and pool, people came to clean the pool early one morning during the stay and were not disruptive at all. There were beach chairs, umbrellas, pool floaties, games, netflix, literally everything you could want or need. Loved our stay!

Really nothing negative to say. We appreciate all extra personal touch the hosts left for us. I wish all ABNB locations had the same care and attention to detail for their guests.

We had a wonderful time. The weather was perfect. The view of the water was everything and was accessible from nearly every room. The home was modern and easily accommodated our large group. Yet it was cozy and beautifully appointed with all the amenities you would ever want. It is ideal for children with every toy imaginable. There was a highchair and a pack and play for our toddler and child appropriate dishes. The kitchen was fully equipped and had 2 sinks, 2 dishwashers and 3 tables for dining. The beautiful pool and hot tub were in constant use. Mary is very thoughtful and assembled a ringed binder with important contacts and suggestions for dining, shopping and entertainment. Although there was no beach on the property there are nearby beaches. The towns of Guilford and (nearby) Madison are charming and well worth visiting. Mary was very accommodating and responded promptly to several inquiries.

Very cute tucked away villa, with pool/hot tub, close to Mohegan Sun. The host was very responsive and the villa was clean and nicely decorated. Would love to come again :-)

This is our second time staying here, conveniently located. Very comfortable accommodation for me and my family. Will definitely stay here again!

Emily and Carol were wonderful hosts. They were responsive to our questions and provided great recommendations. Sitting on the balcony with the view of the trees and the lake beyond was tranquil. The living area is cozily furnished and both the fireplace and tv were easy to use. The nearby community beach was fun to visit and an added benefit of the stay. Great location with plenty of good food and small town charm!

Cabin on Little River met our expectations and more. Myself, 2 sisters and my daughter wanted a quiet getaway. A charming open concept post and beam, pine floors and wood trim, woodstove for winter, deck with charcoal grill. It's very rural and IN the woods ( so bring bug repellant). Even though the host's home is visible you still feel tucked away. Kitchen and bath are modern and clean and the beds and livingroom were very comfortable. The soothing sound of the river is always present. It was relaxing to sit down in the adirondack chairs near its bank. The woods provide a place to walk. Lake is across the road. Glenn informed us of several events nearby that we were really interested in...but we never felt like leaving the cabin! There's a big firepit nearby and wood provided. Glenn is a wonderful host. A fellow artist, I asked to see his studio on the ground level. Even bought a couple small paintings. Do not hesitate to book this place if you are looking for a quiet respite!

We love staying at George’s place, it feels just like home away from home for us. We’ve visited this property several times over the years, most recently with our son who’s now old enough to fully enjoy the yard on his own. He had a fantastic time playing outside, talking to the deer and rabbits that came to visit. We even saw some turkey vultures! Overall a solid place to stay and it’s become somewhat of a family tradition. Thank you George!

My two girlfriends and I stayed at Marianne’s house for a weekend escape, and it was absolutely perfect! The house was clean, cozy, and easy to find. I especially loved the peaceful morning walks to the nearby coffee shop. Marianne was incredibly responsive and offered great recommendations for things to do in the area. Thank you so much, Marianne – we had a wonderful time!

Spacious and comfortable one bedroom + studio, lots of natural light, serene atmosphere, we had a great stay and would be love to visit again

Although this is a basement unit, is is very bright with floor to ceiling windows and a walkout to a beautiful patio. The unit is very clean and located in a beautiful and safe area, close to Fairfield University. It is spacious and comfortable. The unit is just as described and the hosts were wonderful. They left us snacks and light breakfast fare in the fridge. We attended a concert at the Bridgeport Amphitheater and the location of this airbnb was perfect for us. We highly recommend this airbnb and would stay here again.

Jeff’s place was a hidden gem. It was private, close to the beach and town and the home was safe, clean and well designed. Jeff was kind and super responsive. There is a reason this place is always booked. I highly recommend staying here and can’t wait to return!

Beautiful, relaxing, clean Airbnb. Had an issue with the shower, which can happen anywhere, Mk was super responsive and came over quickly. Loved loved loved our stay here. Didn’t use the swimming pool due to weather but the screened deck with the Fire Pit and the superb game room saved the day. Thank you for hosting us will be back

My girlfriend and I had a great stay here. The place was cozy, well-equipped, and perfect for a relaxing getaway. The outdoor area was the true highlight — from the spacious patio to the beautifully maintained landscaping, the property felt peaceful and private. There’s also a pool that looked amazing, even though we couldn’t enjoy it due to the weather. We had some trouble during check-in after a delayed flight and arrived around midnight, but the property owners were just a phone call away and quickly helped us get settled, which we really appreciated. Overall, it was a great experience and we’d absolutely recommend this spot to anyone looking for a quiet, scenic place to unwind.

The pool house is so cute and the outdoor patio is gorgeous and the perfect place to relax. Great place to stay if you want to stay near New Haven but also want to enjoy quiet away from the city. Sue is a responsive and very generous host!

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!

John was a perfect host! Friendly, responsive and made us feel welcome. I took my 9 year old son and we had a great time fishing off the dock and kayaking. The kitchenette is lacking if you want to cook any meals but it didn’t matter in our case. Absolutely beautiful location!

Absolutely perfect. The house provides everything we needed for a great visit. Easy walk to the local beaches. Would definitely return if given the opportunity.

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.