Family-friendly holiday rentals in Fairfield

Great location. Easy check in and out.

Great little spot. Nicely kept and a great spot for a get away.

We had the best thanksgiving trip here! It was beautiful and the space worked so well. We all loved it and would definitely recommend and come back another time! The view of the beach is incredible and lovely walks close by, the little town is cute and it was exactly what we wanted and not too far from the city, but we really felt like we were far away from any of the city busyness it was lovely!

My family was in town for a funeral, and we were able to book Victoria's home and save versus booking multiple hotel rooms. The location is minutes of I-95, so the home gave us a nice, central home base with a kitchen to get to everything and feed the kiddos between events. While we weren't looking for a beach trip - we were able to walk to the local beach and enjoy it with our young kids for a few hours over the weekend. The home was clean, comfortable, and worked perfectly for us. Communicating with Victoria was very easy, and check in/out was a piece of cake as there is a lock box on the house. If I need to bring the family back to the Stamford area, we'll definitely want to stay at Victoria's home again! Thanks!

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!🌅

My parents and I really enjoyed our stay at Mark’s. His house was beautifully situated right on Lake Mahopac with plenty to do in town and in the surrounding area. Everything was as described and met all of our needs. Mark was extremely accommodating with our length of stay (~ 6 weeks) and allowing us to bring our animals (2 dachshunds, 1 cat). Check-in was easy and upon arrival we were greeted with a gift basket and a binder with all sorts of info (emergency, food, fun activities). The backyard was beautiful, completely fenced in, and super convenient for the pups. When we had questions, all we had to do was send off a quick text and Mark responded in a timely manner. I can’t recommend Mark’s place enough!

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

Had a wonderful stay and the host was extremely accommodating. This is the place to be!

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.

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!

This is a lovely little beach cottage! We were very comfortable and had a great time! It was wonderful to have our dog with us! The location is beautiful and private, with access to a very special stretch of beach.

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.

This is a beautiful and peaceful place! Nicely modernized, furnished and decorated apartment in an old farmhouse with lots of charm. A State Park on the beach is a 10min drive away. Our little group enjoyed our short stay here. The place was clean and comfortable and our hosts were very quick and friendly with their responses to our needs. The communication before, while and after was great!

I cannot begin to say enough wonderful things about this hostess and her beautiful properties. I’ve been staying at 2/3 of Jennifer’s properties and each one of them are so incredibly special in their own way. Jennifer is super quick with getting back to me and just beyond accommodating. I look forward to one day staying at her 3rd place, her air bnbs are just so special. A+++

Perfect stay in the coziest cottage! Rose & Jamie were amazing and super helpful and made us feel right at home.

We had a wonderful stay at Todd's place! Todd greeted us warmly and was very responsive. The pool was fantastic and surrounded by beautiful nature, making it a serene spot to relax. We stayed in the pool apartment, which looked out at the pool and stunning backyard. It was well-equipped with a kitchen, pool towels, a TV, couches, and a dining table. Wendy, Todd's wife, welcomed us with cookies, and they provided milk, orange juice, eggs, yogurt, and fruits. There was also a grill available. We stayed for three nights and enjoyed the pool a lot. Despite being a shared pool, there was plenty of space and time for everyone. We also used the tennis court and played some basketball at the basketball rink there. Todd and Wendy made our stay very comfortable and enjoyable. We highly recommend their place!

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!

This place really is a gem. The bedroom and bathroom and spacious and have everything you need. The kitchen is small and can be challenging to work in, but the outdoor grill and dining space make up for that. We spent most of our time outside by the private pool relaxing. James and Margie were great hosts. They greeted us upon arrival and were so friendly and warm. They even brought fresh-bakes cookies. We had a great time!

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.