Family-friendly vacation rentals in Fairfield

Great location. Easy check in and out.

Paula and her place are absolute gems. Communicating with her felt like talking to a friend whose place I was going to be staying at, and it felt like that when we arrived as well. I loved the art and thoughtful touches in each room, and our large group felt cozy yet everyone had their own privacy. The space is actually much larger and more beautiful than the photos even convey! The private trails were stunning and magical— I walked barefoot on the carpet-like moss covered forest paths leading to a Stonehenge-esque clearing with giant boulders. The deck and outdoor space is lovely and has stunning views. So peaceful and quiet with some surprise owl and hawk sightings.

Victoria's place was wonderful! It was spacious and comfortable and gave our family plenty of room to spread out and enjoy our visit. Victoria was a very responsive host and made check in and check out stress free and easy! There was ample parking for our cars and the house was private - it was the "house behind the house" so we weren't subject to busy traffic noise on the street. (Got a little confusing for DoorDash drivers but we worked it out :D). I will book this same place next time I am up for an extended weekend with the family. Highly recommend!

This place was perfect for a city getaway! Me and a couple girl friends went up to the cabin for the weekend and it was so so fun. A beautiful home, and a gorgeous property. Whenever I had questions there was always a very swift response, the grounds keeper is an absolute angel and the kitties running around outside are so fun. Would totally come back!!

We enjoyed a beautiful early spring stay on the farm with a group of 7 ladies, gathering for a chill bachelorette weekend in Cold Springs. The farmhouse was super cozy; great for cooking, crafting, games, tea time, outdoor wine picnics, star gazing at night in the hot tub and making friends with the chickens! A great retreat spot for groups with all the amenities!

We had a lovely weekend at Claudine's. The property is serene. The house is very well equipped and comfortable. We also loved having the sauna. We wanted to grill, but propane was not included in the grill and incurred an extra cost or we had to bring our own tank. For the price and nature of the house, including something like this seems fair. All in all we had a wonderful stay.

What an incredible place! Best location! Hot tub is wonderful! Neighborhood is so quiet! The house was perfect for our group of 7! Comfy beds! Fully stocked house! We will be back next year for sure!!! Amazing times with my friends at this house!! Thank you!!

This home is top notch!! Esther is truly amazing and everything was excellent. The kitchen is amazing, the basement play area was awesome and the rooms were perfect! I will be staying here again!

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.

Viviana is a great host and very helpful. The apartment is very clean and well-organized. The apartment is especially quiet, which allows for great sleeping. Thank you for being such a wonderful host!

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!

Johnny and Amy were amazing hosts. The instructions to park, enter and get in were very well written out before our arrival and check-in was seamless. And once we were there, the place was beautiful, cozy and exactly as described. Our kids loved running around outside in the grass and exploring the outdoor fire-pit. If you want peaceful mornings, laying in bed, watching the wind rustle the trees and listening to the birds sing their morning songs, this is a place for you.

The place is wonderful, had a great cozy stay, the beds are comfortable. Would recommend if you’re looking for a place that’s close by all the restaurants and attractions.

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! 👍🏼

If you want to relax and take in a gorgeous view, this is the place! The apartment is huge; you can really spread out. The two living areas have that stunning view over the Hudson. Looking at a map, we think there's a state park opposite the Airbnb, so there's no development, just trees on the hillside. The weather was closing in, so we didn't get the gorgeous sunset we'd hoped for, but you might. We did takeout so that we didn't have to leave the view. Brothers Fish & Chips was a total delight -- the fish was fresh and lightly battered. Very much like you get in England! And the hosts provided breakfast items, a real bonus. Two things to note -- commuter trains run between the property and the river (but below the level of the apartment) and Sing Sing prison is within view. We weren't bothered by either, especially since there aren't many trains at night and you don't see them from the patios. And driving along the prison road to pick up our takeout was more interesting than scary.

Very nice place and location is amazing. We were grateful that our host provide some basic amenities - coffee, shampoo and condtuoner, etc. Made our visit easy and very pleasant. Thank you!

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! ☺️

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

Gaby’s place was clean and comfortable! She is very kind and it was exactly what we needed for the week. Her check in instructions and directions were thorough and the home is in a beautiful area. Already have our next stay booked :)

Michael was a great host, friendly, flexible and helpful. The house is beautiful and has all the amenities you would expect. We loved staying there and would definitely like to stay again.

Truly home sweet home. Just walk in and relax. Fully stocked kitchen including milk, eggs, butter and pastries so no need to rush out to go grocery shopping. Convenient to New Haven yet completely quiet neighborhood for resting and taking walks.

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 house was exactly what our group was looking for. It sleeps 12 people comfortably and it’s very large. A quick walk from the jitney with 5 parking spots, it was perfect for all guests and their respective method of transportation. The backyard is also VERY spacious. There’s a grill, tennis court, etc. plenty of things to do — there’s never really a reason to leave during your stay. The house also has really nice energy. It’s quaint, gets beautiful light and is really charming! I would stay here again :)

We loved our stay at Sarah’s home . It was the perfect end to the last week of summer . The pool and outside area/garden are lovely , lots of sunshine and a good amount of shade coverage due to beautiful trees in the afternoon. The bedrooms were great , lots of light , very comfortable beds good amount of closet space and a great set up all around . Sarah is a gracious host and has thought of every detail to make her guests stay enjoyable . Quick to respond and check in , and an absolute pleasure to work with . Thank you for a wonderful stay , look forward to returning soon .