Family-friendly holiday rentals in Fairfield

Great location. Easy check in and out.

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!

The house was lovely and very clean and Piotr was an excellent host and even met us at check in to show us around. There are 4 bedrooms and each bedroom has its own bathroom which was very convenient for us. The kitchen was well stocked and It was very comfortable stay for my family of 7 adults and two babies and two dogs. One bedroom is on the main floor and two bedrooms are on the walkout lower level and one bedroom is on the upper floor. To get to the upper floor there is a steep winding staircase that wasn’t an issue for us, but I would not recommended it for small children or toddlers. The outdoor hot tub was a nice addition.

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!

Jim and Heather’s house was a wonderful escape from NYC. We loved sitting by the fire, relaxing in the hot tub, reading in any number of nooks, cooking meals, taking winter walks in the backyard trails and taking lovely nearby hikes. Jim and Heather were proactive with their information, checked in to see how things were going, and responded quickly and helpfully when we had questions. From the minute we arrived, we felt at home, and it really seemed like that what was Heather and Jim hoped would happen.

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.

Place was very nice and organized very well thought out rules were easy to follow and the view was out of this world.

We loved our stay at the "tree house", you're literally among the top of the trees all around. Our favorite place was the large wrap-around deck with very comfortable couches and dining table. We ate all our meals outside for 18 days. Gorgeous views and sunsets. Beach access was 5 minutes down a private path, leading to an almost private beach. Another favorite place was the hot tub, a big hit for out grandkids. There was also a sauna, which we did not use. Cee responded to our questions within 10 minutes, even from Europe. ..great host.

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.

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.

We loved our stay at Jonathan’s place. He was proactive and flexible with our late check in time which I really appreciated. The apartment was exactly as described/in the photos, peaceful, and very comfortable. Will definitely be staying again!

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!

We had such a great time at the cottage. The place made our trip perfect. Thank you Jennifer for being such a kind and communicative host! The place looks just like the pictures and feels so homey. We loved every second of staying here, we will be back again!

This was a great place for,my family to stay while visiting in Central CT. Very walkable to downtown Middletown with restaurants and shops. Monica was very responsive to any inquiries. And a great place to stay with a dog!

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

Great place and location. Tony was very helpful and everything from booking to checking in and checking out was all outstanding. Thanks!

Nice, quiet spot in a lovely small town in Connecticut. Well appointed and short drive to everything in the area.

Thank you for being the official host of Santa and Mrs Claus this holiday season! They really enjoyed their stay! Robert was a great, friendly host—super helpful and accommodating, especially with getting Santa checked in. The property was exactly as described, with clear instructions that made their stay seamless. Would recommend the property and host

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 was in town for work and Gaby's place was perfect. It's a lovely finished basement apartment in a beautiful home in Stony Brook. Perfect for a single person or couple looking for a comfortable, affordable, and safe place in the area. I would absolutely book again if I needed to.

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.

Great vacation…the house and pool were very enjoyable and relaxing. The pool was always heated, the host was always responsive and the area was close to some great restaurants and beaches. Thanks again

This was our third stay at Marybeth's, everything was great, as usual. The unit is spacious, clean, and very conveniently located.

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.