Family-friendly holiday rentals in Fairfield

My family enjoyed their short stay at Camilla’s apartment. The apartment was a beautiful place.

We loved this place! So peaceful and quiet. Lovely beach to walk to. Very responsive hosts- had a slight issue with hot tub and it was handled very quickly and then someone brought us a the best coffee cake. This place felt like the best of Long Island and we are thankful to have stayed!

My family of 8 adults needed a place to stay near a wedding at Glynwood. This wonderful spot was minutes away from the farm and town. The number of bedrooms and bathrooms gave everyone the privacy desired while the well equipped kitchen and living rooms had plenty of space for gathering. The house and land are beautiful, including the trail. Paula was easy to communicate with and my whole family felt comfortable and happy with the spot. Highly recommend!

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!

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!

We were all immediately happy at Susan’s place! Our two year old found the toy room and played happily, our eleven year old lived in the beautiful pool and my husband and I felt like we could really relax. The location is 5 minutes from town where you can get coffee and a bite, or 8 minutes from the beach/state park. The property feels private and the house is charming and well appointed. The pictures don’t do it justice, it’s really lovely.

We had a wonderful stay! Gabe was a very welcoming host and shared some great local restaurant recommendations—highly recommend checking out Casa Nova on River Road. His two dogs, Molly and Nate, were also incredibly friendly and added a warm, homey touch to the experience. The apartment was spotless and filled with thoughtful notes that made everything easy. A special surprise was the bag of everything needed to make s’mores left for us—such a sweet and thoughtful gesture! The pool area offered stunning views, and the hot tub was clean and perfect for relaxing. There’s even a hiking trail accessible right from the property, which we unfortunately didn’t get a chance to explore—but it’s a great bonus for future visits. This place truly felt like a little piece of heaven. We’d absolutely stay here again!

We had a wonderful time. The weather was perfect. The view of the water was everything and was accessible from nearly every room. The home was modern and easily accommodated our large group. Yet it was cozy and beautifully appointed with all the amenities you would ever want. It is ideal for children with every toy imaginable. There was a highchair and a pack and play for our toddler and child appropriate dishes. The kitchen was fully equipped and had 2 sinks, 2 dishwashers and 3 tables for dining. The beautiful pool and hot tub were in constant use. Mary is very thoughtful and assembled a ringed binder with important contacts and suggestions for dining, shopping and entertainment. Although there was no beach on the property there are nearby beaches. The towns of Guilford and (nearby) Madison are charming and well worth visiting. Mary was very accommodating and responded promptly to several inquiries.

Noel’s third floor apartment is light-filled, spacious, has a cute rustic vibe and is perfectly located. It’s across the street from East Rock Park (great for walks and runs) and walking distance to restaurants and an ice cream shop. The entrance to the apartment is through Noel‘s home – – no private entrance. Parking was incredibly easy—right on the street in front of the house! We enjoyed our stay very much, especially thoughtful touches like breakfast muffins and coffee. The apartment is full of interesting books and games and is very comfortable. Noel is a helpful host.

Clean, spacious, private basement apartment with some natural light. Very comfortable bed. Lovely backyard. Quiet, green residential neighborhood. Within 10 minute driving distance from Port Jefferson town center.

Kate and Daniel are wonderful! Their beach cottage is a must for all families. The farmers markets within 2 miles have all the produce you need, while the fish markets within 5 miles have all the fresh caught seafood you need! There are several New York vineyards nearby and I’d recommend traveling to all the local towns like Greenport, Shelter Island, West/East/South Hampton, and Montauk to see how each one has its own identity. Overall, my wife and I loved our stay at the cottage and we spent most are days laying on the back porch with the beautiful views! Also, great kitchen for cooking and backyard grill with a view.

This is our second time staying here, conveniently located. Very comfortable accommodation for me and my family. Will definitely stay here again!

This was a lovely cottage and location, part of a private beach community, on a very quiet road, with partial views of the Long Island Sound. Gail was thoughtful to put out a nice welcome basket and some cold sodas and bottle water in the fridge. Perfect spot for two to three people. Close to Guilford main green, dock and nearby Stony Creek and Madison. We didn't make use of the bikes and kayaks bc it rained in the mornings, but we enjoyed one of the two beach just a few minute walk away. Jacob's cove area is a gem.

Victor and Kim were gracious and amazing hosts. I was celebrating my birthday and they even had a card, a bottle of champagne, red wine and fruit. It was such a wonderful surprise! The house was so beautiful and the beach is just outside! The kitchen was fully stocked with everything one would need to cook for a family; there was a convection oven! We loved using the grill as it was memorial day. Bathrooms had rain showers. Beds were so comfortable and it was truly wonderful to wake up to a beautiful sunrise and to just listen to the waves from the deck or even the living room. We spent a lot of time outside, on the beach. It was home away from home.

As described, a charming, comfortable home on a beautiful property in a convenient yet peaceful very "New Englandy" neighborhood The house is a great place to spend time arfeceive friends, really well appointed from kitchen gear to a playroom that is made for toddlers, very comfortable sitting areas with lots of light and the bedrooms that are all quite comfortable and give all a nice level of privacy. Deirdre was a top notch host, always responsive and accommodating. No hesitations in recommending her house - probably our best Airbnb experience to date. Hope it will be available for our next visit to the Stamford area.

Jamie & Rose are the consummate hosts: clear communicators, friendly, helpful and supportive of their guests' (and their animals') experience. The cottage is New England cute on steroids, and super private. All was tip top, first rate for a country cottage experience. Thanks for making our experience so smooth and relaxing.

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!

My girlfriend and I had a great stay here. The place was cozy, well-equipped, and perfect for a relaxing getaway. The outdoor area was the true highlight — from the spacious patio to the beautifully maintained landscaping, the property felt peaceful and private. There’s also a pool that looked amazing, even though we couldn’t enjoy it due to the weather. We had some trouble during check-in after a delayed flight and arrived around midnight, but the property owners were just a phone call away and quickly helped us get settled, which we really appreciated. Overall, it was a great experience and we’d absolutely recommend this spot to anyone looking for a quiet, scenic place to unwind.

Rob’s place is very comfy with all the little things you could wish for. He even left snacks. The downstairs apartment is very private. His description was very accurate, with a mild smell of mold that clear out after starting the AC and air filter. I’m allergic to mold and had no problems. I would gladly stay again.

The pool house is so cute and the outdoor patio is gorgeous and the perfect place to relax. Great place to stay if you want to stay near New Haven but also want to enjoy quiet away from the city. Sue is a responsive and very generous host!

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!

Jeff's place has a lot of character and is spacious. The setting is excellent, near the water, with Satterly Landing right down the road. We enjoyed our stay.

This is a fantastic and charming historic property with all of amenities you could ask for. Kate was super accommodating with all if our requests. It made our little family reunion one of the best! Thank you Kate!

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 .