Family-friendly vacation rentals in Fairfield
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Top-rated family-friendly rentals in Fairfield
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
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Popular amenities for Fairfield family-friendly rentals
Family-friendly home rentals with a hot tub
Apartment in Downtown New Haven
4.75 out of 5 average rating, 139 reviewsLuxury Penthouse Minutes to Yale
Good location host is very communicative
Home in North Fork
4.94 out of 5 average rating, 17 reviewsChic Beach House: Waterfront, Vineyards, Hot Tub
I absolutely fell in love with this place and location. The beach is at your back door. Great restaurant within a few feet of the house. No need to leave the house. Everything is supplied for you. Super clean, beautifully decorated and the most beautiful, peaceful sunsets you could ever hope for. I can’t wait to rebook!!! Wish I could have stayed longer. The property manger was super nice and very accommodating. It was one of the best places I’ve stayed at!
Villa in Hopewell Junction
4.96 out of 5 average rating, 289 reviewsThe Mission House Sanctuary
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.
Home in Stormville
5 out of 5 average rating, 11 reviews2 MasterSuites Heated SaltWater Pool+HotTub&More
Beyond thrilled with a house you have see to believe. Best hosts we've ever had by far. Paul went above and beyond for us, even enlisting the help of his son to help our son with a video game issue! The house is perfection and we can't wait to come back. This is one-of-a-kind!
Home in Shippan Point
4.94 out of 5 average rating, 114 reviewsOCEAN COAST LUXURY BEACH HOUSE/45 min to NYC
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!
Home in Branford
4.88 out of 5 average rating, 68 reviewsAmazing Waterfront Home, Private Beach & Hot Tub
Wonderful home and location. The house was better than the photos. The host was very friendly and made the whole process simple and enjoyable. I would highly recommend.
Home in Putnam Valley
4.99 out of 5 average rating, 74 reviewsThe Lodge of Putnam Valley w/hot tub/pool/grounds
Jim and Heather were kind and accommodating. Their place was great with so much to do and explore. We couldn’t have asked for better hosts.
Apartment in Shelton
4.68 out of 5 average rating, 323 reviews1ST FLR APT Your private resort, now FAMILY-ized!
Place was very nice and organized very well thought out rules were easy to follow and the view was out of this world.
Family- and pet-friendly home rentals
Apartment in East Rock
4.9 out of 5 average rating, 208 reviews3 RM Apt. w/kit. in historic house
such a cute place for a getaway! it was perfect and the host was extremely helpful, knowledgeable about the area, and nice! also, don’t go grocery shopping before seeing the food that noelle has in the apartment! we underestimated the food that she provides. we definitely want to come back at some point for another trip :)
Cottage in Middlefield
4.92 out of 5 average rating, 244 reviewsLake Beseck cottage
I love staying at Elisabeth’s place! It has become my “home away from home”. Cozy, comfy and just perfect!
Cottage in North Fork
4.97 out of 5 average rating, 150 reviewsSavor Blazing Ocean Sunsets at a Soothing Beachfront Haven
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.
Guesthouse in South Salem
4.94 out of 5 average rating, 267 reviews1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt
We had a great stay at Jonathan's apartment in South Salem. We loved the historic setting. It is a beautifully designed space with unique touches throughout. Jonathan communicated before and during our stay to make sure we had everything we needed. We would happily stay again!
Apartment in Milford
4.87 out of 5 average rating, 262 reviewsThe Farmhouse Estate Apartment
Great stay at the farmhouse! It was the bottom floor. We only needed two of the three rooms. The bathroom was in the back with the kitchen. It’s an old house but very modern interior. Just what we needed!
Cottage in Port Jefferson Station
4.8 out of 5 average rating, 433 reviewsThe Red Cottage Circa 1936
Jennifer was a gracious host. We had everything we needed for a perfect stay. Highly recommend! Thank you for hosting us! Joe and crew
Apartment in Ossining
4.95 out of 5 average rating, 392 reviewsHudson River Peaceful Getaway, Explore from here
This is a great place to stay. It was clean, comfortable, had everything I needed, with an incredible view of the Hudson River. Further, the owner lives upstairs and was very responsive to my needs. And, the house is located within three minutes by car of a shopping center with everything that you need. Will definitely come back. Very happy that I chose thislocation.
Cottage in Redding
4.93 out of 5 average rating, 257 reviewsCozy Cottage by the pond
Perfect stay in the coziest cottage! Rose & Jamie were amazing and super helpful and made us feel right at home.
Family-friendly home rentals with a pool
Apartment in Redding
5 out of 5 average rating, 17 reviewsPoolside apartment with private tennis court.
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!
Barn in Bethel
4.98 out of 5 average rating, 223 reviewsEscape to a Restored New England Antique Milk Barn
My wife and I spent a long weekend here and had a great stay. the cottage is as exactly as described, and we felt right at home. it was clean, comfortable and a peaceful retreat. the jetted bathtub was AMAZING and the loft space was spacious with a gorgeous & comfortable bed. we will definitely stay again if we come back to the area!
Home in Stormville
4.94 out of 5 average rating, 178 reviewsPrivate Hudson Valley Country Retreat
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
Home in Stony Brook
4.93 out of 5 average rating, 512 reviewsSpacious Studio Apartment- near SBU
Gaby's apartment was so cozy, clean, and exactly what we needed for our Thanksgiving trip. The area is peaceful but also easily accessible to the highway and Stony Brook, a cute, walkable North Shore village. There's a ton of lovely nature spots all along the shore we were able to check out in between our holiday plans for some peaceful moments. Most importantly, Gaby was so responsive and went above and beyond to have the apartment ready much earlier than check-in time--and on Thanksgiving no less! It really helped us with travel plans and made our stay that much more enjoyable. The bed is cozy, the room is warm and comfy, and the amenities were top notch. Thanks again so much Gaby!
Home in Cheshire
5 out of 5 average rating, 130 reviewsPool House
Sue was a wonderful hostess. She left us fresh pastries, milk, eggs and water. The accommodations were very clean and comfortable. Would highly recommend the Pool House to anyone wanting a nice comfy stay.
Home in Monroe
4.96 out of 5 average rating, 199 reviewsGarden Level Suite with Beautiful Pool
This was our third stay at Marybeth's, everything was great, as usual. The unit is spacious, clean, and very conveniently located.
Cottage in Redding
4.95 out of 5 average rating, 22 reviewsGuesthouse & private pool, historic 24-acre estate
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!
Home in Yorktown Heights
4.88 out of 5 average rating, 8 reviewsHoliday Escape to Victorian Farmhouse Getaway
Enjoyed the comfortable and quiet tranquility of the place. Stayed over a month. Especially the beautiful Fall foliage of the surrounding area had offered during our stay. Marisa was a wonderful host and easy to communicate. Appreciated her quick responses to resolve when we encountered some glitches in the beginning. Although, We didn’t get to use her pool being out of season, it would have been nice. Glad we were able to make this home away from home with ease.
Quick stats about vacation rentals that are family-friendly in Fairfield
Total rentals
200 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
3.8K reviews
Pet-friendly rentals
90 properties allow pets
Rentals with a pool
30 properties have a pool
Rentals with dedicated workspaces
120 properties have a dedicated workspace
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