Family-friendly holiday rentals in Old Saybrook

There is nothing more frustrating than not being able to have a decent shower while you are on vacation. That was absolutely not the case here. The hot water and water pressure in both bathrooms was exceptional. This is a great place in a great area. We will definitely try to get back here.

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.

This is the 2nd Thanksgiving weekend we spent at Deeanna's. Her home is beautiful, comfortable and each detail is thought though in the best way. Deeanna went above and beyond to accommodate my family and we are so grateful to her. The kitchen is perfection and the bedrooms are lovely and comfortable. The scenery and views are breathtaking. Overall, this home is a total gem. Thank you, Deeanna! We hope to come back next year!

This getaway was very last minute and there was huge importance on it because I needed some time away and because I had never booked an Airbnb before. I wanted to make sure that my family and I were able to be someplace peaceful and have a really good time and Brian’s home provided just that. The stay was so much more than we expected and Brian was absolutely amazing. He’s super responsive and accommodating. Hoping to stay here again in the near future!

We had such a nice time at Tracey and Patrick's. The house was perfect for our family and two little dogs. There was plenty of space for everyone, and anything we could've possibly needed was there and easy to find. The location was perfect in a nice quiet neighborhood that was just a short distance drive from anything you might want to do during your vacation. What a wonderful . We all agreed we would definitely like to visit again and would certainly stay at Tracey and Patrick's if available. Thank you so much for all the great memories! Jen & Co.

We had a fabulous time! Can't wait to come back. Was equally perfect for two toddlers as it was for four adults! Beautiful property, amazing hot tub, comfortable beds, great kitchen... everything was lovely.

Cozy and pretty home, all ready for a chill weekend. Cindy is super nice and easy to work with. Very generous too. The 2 pups loved the fenced in yards. Kitchen/dining room space is big and bright and awesome to hang out or read in the corner nook. I am sure the backyard and pool would be great in summer. Beds were comfortable. Thank you Cindy!

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!

This was a fabulous destination! We were looking for a big place to have a special anniversary party weekend with extended family, and this house had everything we needed. Plenty of bedrooms upstairs and first floor, many common gathering areas, large kitchen and dining room tables, and lots of Space. (And this doesn't even include the explorable property outside.) The dozens of photos in the listing were very helpful, as well as the detailed descriptions. We had specific needs for elderly relatives with disabilities, and owner Lynne was so responsive in her replies to my many messages with varied questions. Truly, Lynne, you deserve a gold star from Airbnb for promptness and offering up ways and help that made our stay both easier and fulfilling.

I fell in love with this apartment, the living room, kitchen, bathroom and bedroom were excellent, very cozy and endless amenities, the only complaint I have is the ceiling of the room but it is understandable and is not a big deal and they did not tell us where to put the garbage so we had to leave it in front of the door in the garage but other than that a very good experience in this beautiful place, I recommend it!

Was in the area to visit family and this was a perfect location for me. Had just what my family needed to have a great weekend

This was a great find! I booked this Airbnb for myself and 4 other girls and there was plenty of room and space for us to hangout, sleep, and get ready. Walkable to town. Extremely clean and had all the amenities you would need for a short weekend getaway. Marianne and Steven were very responsive whenever I had a question. I would totally book this Airbnb again!

My daughter and I loved our stay so much. The setting is so beautiful and peaceful. I loved listening to all the bird song and my daughter loved the fish! Such a cozy, comfortable home. We loved our relaxing time here. Gabriele is a fabulous host, so responsive and so kind. Thank you!!

My husband and I had a wonderful 3-day stay with our 6 year old granddaughter. She enjoyed making herself at home in the lovely space. Nice deck and grill for eating in the evening. She especially loved all of the animals from the dogs and cats to the emus. She enjoyed learning their names, feeding them and watching l, interacting or tagging along with the owners and various caretakers. Everyone was so kind and welcoming. There is a great playground, various hiking and restaurant options, and a fantastic public library in Simsburg. Highly recommend!

We had a wonderful stay at Steffen & Sara's charming bungalow! The location was incredibly convenient, check in was a breeze, and the house was comfortable, well-appointed, and inviting. The house was meticulously clean and well-maintained. Steffen & Sara were incredibly responsive and accommodating, making sure we had everything we needed for a great stay. We would absolutely stay here again and highly recommend it to anyone looking for a great place to stay in the area!

Tricia and her husband were so lovely! They were super responsive, kind, friendly, and went above and beyond to make us feel welcome. The cottage was super cozy, clean, and pet friendly. Our dogs loved the private outdoor space. The location was also excellent - a short drive to town in Southampton and Westhampton. Would highly recommend and will definitely be booking again in the future!

Friendly and prompt responder. Really clean. The kids more than loved the game room. And I personally loved the decor. Only objection is it’s kinda out of the way and you’d have to drive to do any activities, but other than that a really great stay.

We had an amazing stay at Sally’s place in Bethel! My fiancé and I visited CT for the first time to celebrate my birthday and go to a convention nearby. This cottage was perfect for the two of us. The host was very responsive and accommodating as well! The cottage was in pristine condition, the house manual was very easy to follow, the recommendations were great, the scenery was out of a movie, and my favorite part was the hot tub in our restroom which was perfect after a long day! We had a great time and would love to come back again! Thanks for your hospitality Sally! ☺️

We had a wonderful stay. Cute and comfortable house in an amazing location. Very comfortable for a family of 4.

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!

This was our first time at the Barn. There were 8 of us. We had plenty of room. Plenty of parking. MaryBeth and Doug are extremely friendly. We enjoyed hearing about the history of the Barn. Will definitely book there again next year.

Wonderful time staying at Milton and Megan's. The location was perfect and the home had everything we needed and more to work remotely for the week. Thank you!

We had a wonderful two day stay at Roger and Amy’s place. It was fantastic- such a beautiful, inviting home. Our kids had a blast in the heated pool- we could barely get them to come out despite it being under 60 degrees out! The kitchen was stocked with more than just kitchen basics- the spice cabinet had soo many different choices ! It was probably the most perfect AirBnb experience I’ve had and we travel plenty.

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!