
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.
Vacation rentals for every style
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Popular amenities for Fairfield family-friendly rentals
Family-friendly home rentals with a hot tub

Luxury Penthouse Minutes to Yale
Great location. Easy check in and out.

Dunes Beach House: Hot Tub and Steps to Beach
Great little spot. Nicely kept and a great spot for a get away.

Chic Beach House: Waterfront, Vineyards, Hot Tub
Our family rented for a weekend off season. Surroundings were beautiful. Home was clean and comfortable. Host was super friendly and very communicative. Any questions were answered within 5-10 minutes. Lots and lots of space for large groups. We had 6 adults, 2 children and a dog in our trip. Literally open the back door and you’re right on the beautiful beach!

OCEAN COAST LUXURY BEACH HOUSE/45 min to NYC
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!

The Lodge of Putnam Valley w/hot tub/pool/grounds
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!!

Lake Life in beautiful updated Lake House
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!

1ST FLR APT Your private resort, now FAMILY-ized!
It was great. Everything was the complete opposite of what I expected

Ensuite with private entrance
Had a wonderful stay and the host was extremely accommodating. This is the place to be!
Family- and pet-friendly home rentals

On the Park: 3 RM Apt. w/kit. in historic house
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.

The Palm Tree Extended Stay
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!

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven
We absolutely loved our quick getaway from the city at Kate’s lovely home. It is hard to articulate in words just how beautiful of a home and location this was. It was truly magical. We were very comfortable as a family traveling with young children. Despite the weather being a bit chilly, we had a wonderful time soaking the views and discovering “treasures” by the water. We cannot wait to come back again soon.

1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt
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 Farmhouse Estate Apartment
This was the perfect place for our family to stay! There was plenty of space and everything we needed was provided. We would definitely stay here again!

Hudson River Peaceful Getaway, Explore from here
This is a wonderful place to stay. It is clean, comfortable, close to services and has a fantastic view with lots of natural scenery. Dan and his wife are exceptional hosts and extremely responsive to the needs of their visitors.

3 bedroom near Wesleyan, downtown
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!

Cozy Cottage by the pond
My husband and I had a great stay. James and Rose are super helpful hosts. It’s a great place to relax and enjoy nature. Walking distance to a lovely park they recommended with tons of hiking trails and very quiet.
Family-friendly home rentals with a pool

Escape to a Restored New England Antique Milk Barn
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! ☺️

Private 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

Spacious Studio Apartment- near SBU
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 :)

Pool House
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.

Garden Level Suite with Beautiful Pool
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!

1856 Trading House close to water
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.

* Overlook the Reservoirs Custom Victorian Farmhse
We had an incredible stay at this beautiful home for the holidays! The house is spacious and immaculately decorated, with thoughtful touches that made it feel warm and inviting. The layout was perfect for hosting our family gatherings, with plenty of room for everyone to spread out and relax. The kitchen was fully equipped, making meal prep a breeze, and the cozy living areas were ideal for relaxing.. The quiet suburban setting offered a peaceful retreat, while still being close to everything we needed. We couldn’t have asked for a better place to create lasting holiday memories. Highly recommend!

Newly-Renovated, Private, 4BR Cape w/Pool
Great home and host. Responsive to inquiries. Would recommend!
Quick stats about vacation rentals that are family-friendly in Fairfield
Total rentals
210 properties
Nightly prices starting at
$69 CAD before taxes and fees
Total number of reviews
4.3K reviews
Pet-friendly rentals
80 properties allow pets
Rentals with a pool
30 properties have a pool
Rentals with dedicated workspaces
130 properties have a dedicated workspace
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- Radio City Music Hall
- Times Square
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Barclays Center
- Tenement Museum
- Riverside Park
- Comedy Cellar
- Yale University
- Apollo Theater
- Gilgo Beach
- St. Nicholas Park
- Citi Field
- Yankee Stadium
- Inwood Hill Park
- MetLife Stadium
- Bronx Zoo
- Astoria Park
- United Nations Headquarters
- Dunewood
- Rockefeller Center