Family-friendly vacation rentals in Fairfield

Absolutely STUNNING cottage. I share the sentiment of other guests in just how beautiful, clean, cozy and comfortable this space is! Stocked kitchen, lovely bathtub, pristine clean bathroom (and everywhere) and fast and strong wifi in the whole house. About 100mph internet speed. The bedroom was SO COZY and the bed was so comfortable. Felt super private for being next to the main property. Friendly and responsive hosts! Gorgeous property. One of the overall best places I’ve stayed.

Place was perfect! Clean & made our Holiday stay in the beautiful Hudson Valley a wonderful experience. We loved the personal touches the house offered and we will be back

I had a great stay here and the place felt like home immediately. There was a lot of space for my dog to run around as well. Everything was very clean and organized. There was noise through the apartment as per previous reviews as there are other people living throughout the house, but it is something I did not mind at all, especially since I had my dog with me.

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!

The space is adorable, and we loved the history of the rental and the community. The location was perfect for us—close to everything and secluded all at the same time. Also Jeff is an amazing host and made us feel welcome/at home. The next time we have to head to NY for a family visit we will definitely try to stay here again.

We had an incredible stay at this beautiful home for the holidays! The house is spacious and immaculately decorated, with thoughtful touches that made it feel warm and inviting. The layout was perfect for hosting our family gatherings, with plenty of room for everyone to spread out and relax. The kitchen was fully equipped, making meal prep a breeze, and the cozy living areas were ideal for relaxing.. The quiet suburban setting offered a peaceful retreat, while still being close to everything we needed. We couldn’t have asked for a better place to create lasting holiday memories. Highly recommend!

Great home and host. Responsive to inquiries. Would recommend!

Awesome place for a huge group. I had a group of 10 and it is walkable to downtown where the bars and restaurants are. Easy in and out, perfect for a night or two in New Haven.

I had an amazing stay at this Airbnb! Henri was incredibly responsive and made sure all of my questions were answered promptly, which made the whole process seamless and stress-free. The home itself was spotless, well-maintained, and had everything we needed for a comfortable stay. It was spacious and thoughtfully stocked with all the essentials, from kitchen items to fresh linens. I felt right at home from the moment I arrived. Highly recommend this place if you're looking for a welcoming, comfortable, and well-equipped spot to stay!

Camila was a great host, very responsive and always helpful. The apartment was clean, tidy and cosy and made us feel at home very quickly. Location was good, walkable distance to New Haven Green and its surroundings. All in all, we enjoyed our stay very much and would recommend Camila’s place to anyone planing to spend some time in New Haven.

Bill’s place provided a wonderful location for our family of seven to spend our Thanksgiving holiday. The house was clean, uncluttered, and comfortable in every way. The kitchen had everything we could hope to find for meal preparation. The two sitting rooms provided delightful spots for reading, conversation or catching up on the television news. The upstairs bathroom was especially room and well-appointed. While it was winter when we visited, we could tell that this house would be a truly marvelous spot during the summer months as it had a great back deck and was truly only a hundred yards or so from a beach on the Long Island Sound. While it may not be the first choice of those who are on a tight budget, we recommend this home highly.

This was the perfect weekend getaway - the house is cozy and beautiful, the neighborhood was lovely, had incredible views and offered so much to see and do. The fireplace was amazing, great kitchen with everything you need and the host was highly communicative and helpful. I can't wait to return!

Andy's place was impeccably clean and well-appointed. I cook most of my meals while traveling and the kitchen was well stocked with the basics (oils, spices, soy sauce, vinegar) and all the necessary cookware (including containers & wrap to store leftovers & prepped food items). It was the type of Airbnb that felt more like visiting the home of a friend who had thoughtfully considered anything you might need. (including detergent for laundry & toiletries). This was refreshing in light of many Airbnb's feeling more like a Residence Inn, than a home. As a bonus, Andy has excellent taste in books and I wished my stay was longer so I could have read some of what was on the shelves.

After an initial snafu with my booking through the app, Debbie sprung to action, contacted me, and upgraded us to this house, which was even nicer and closer to the ocean than the house I originally wanted to book. I thought she handled what could have been a very upsetting situation extremely well and overcompensated for us, if anything. Place and location were wonderful. Definitely recommend.

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

The house is absolutely lovely and well-maintained, and Jonathan is extremely helpful, responsive, and kind. I had an enjoyable and easy weekend with family members, and would highly recommend this property, which is very authentic to the setting, to anyone considering a stay in the area.

Stan’s place was perfect for the trip. The place was clean, the location was convenient, and there was plenty of space. The extra amenities and friendliness of the host made us feel right at home. I would definitely stay there again.

Margie’s place is an amazing hidden gem. The inside is very clean and comfortable. The outside is an experience of its own. The lake will drop your blood pressure immediately. Gorgeous surroundings. The dogs are friendly and lovable. We will be back! 👍🏼

A Perfect Beach Getaway! Wow, this place was amazing! The pictures online are great, and it's even better in person. We stayed in January, and it was the perfect escape: incredibly relaxing and quiet. The views are breathtaking. We were treated to stunning sunrises each morning and enjoyed stargazing at night from the decks, all while listening to the soothing sound of the water lapping on the shore. The home is beautifully decorated with a beachy theme that feels just right—tasteful without being over the top. The welcome waters in each bedroom, along with the fruit and wine, were such thoughtful touches that made us feel right at home. The house was fully equipped with everything we needed and was impeccably clean. Victor and Kim were very accessible and made sure we had everything we required for a comfortable stay. The location is also very convenient, with plenty of shops and restaurants nearby. Overall, we had an unforgettable experience and can’t wait to return!

We can't say enough positive things about TJ and his beautiful home on the beach in Milford… There isn't anything he hasn't thought of and the pictures don't even do it justice. My family and I were blown away at how comfortable and beautiful the experience was; we didn't wanna leave. As a host myself of several properties, TJ really sets the standard; his home's layout is amazing and the view of the water is unobstructed from the hot tub, from every room in the house and even the rooftop deck. We can't wait to go back! Be sure to wake up for the sunrise!🌅

A perfect stay for our family of four for a fall weekend out of the city. Loved everything about the property and home. Absolutely stunning surroundings and the house had everything we need. Can't wait to come back!

Shay’s location is a slice of heaven. The views and sunrises/sunsets are unparalleled! The house itself is comfortable and clean. My family spent Christmas here and we really made the it our own for a few days. We spent most of our time upstairs. The kitchen has most everything you’d need for cooking big meals. I also appreciated the toys, games, and humidifiers. My one year old enjoyed the toys and when he came down with a cold, I was very grateful for the humidifier. Shay was extremely communicative and accommodating. We checked in early and out late which we really appreciated and needed. We experienced the coldest temps of the winter during the our stay and when the downstairs family room was extremely cold, Shay provided extra space heaters which did the trick. I recommend Shay’s home! It met our needs and Shay’s welcoming nature was an added bonus.

Absolutely loved Amanda and Rick’s place. We are so so so happy we were able to spend a few days there with family! Thank you guys so much!