Family-friendly vacation rentals in Fairfield

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Fairfield family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Apartment in Downtown New Haven
4.75 out of 5 average rating, 140 reviews

Luxury Penthouse Minutes to Yale

AmandaRating, 5 stars3 months ago
Great location. Easy check in and out.
Home in Rocky Point
4.78 out of 5 average rating, 9 reviews

Dunes Beach House: Hot Tub and Steps to Beach

TrevorRating, 5 stars35 months ago
Great little spot. Nicely kept and a great spot for a get away.
Home in North Fork
4.95 out of 5 average rating, 20 reviews

Chic Beach House: Waterfront, Vineyards, Hot Tub

SamRating, 5 stars3 weeks ago
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!
Superhost
Home in Shippan Point
4.94 out of 5 average rating, 115 reviews

OCEAN COAST LUXURY BEACH HOUSE/45 min to NYC

DebraRating, 5 stars1 week ago
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!
Top guest favorite
Home in Putnam Valley
4.99 out of 5 average rating, 77 reviews

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

GeorgiaRating, 5 stars3 months ago
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!!
Home in Mahopac
4.87 out of 5 average rating, 47 reviews

Lake Life in beautiful updated Lake House

CybilRating, 5 stars7 months ago
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!
Apartment in Shelton
4.68 out of 5 average rating, 324 reviews

1ST FLR APT Your private resort, now FAMILY-ized!

MichaelRating, 5 stars4 months ago
It was great. Everything was the complete opposite of what I expected
Guest suite in Wilton
4.76 out of 5 average rating, 50 reviews

Ensuite with private entrance

NicholasRating, 5 stars10 months ago
Had a wonderful stay and the host was extremely accommodating. This is the place to be!

Family- and pet-friendly home rentals

Superhost
Apartment in East Rock
4.9 out of 5 average rating, 210 reviews

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

NathanielRating, 5 stars2 months ago
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.
Superhost
Apartment in Port Jefferson Station
4.84 out of 5 average rating, 288 reviews

The Palm Tree Extended Stay

BethRating, 5 stars3 days ago
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!
Guest favorite
Cottage in North Fork
4.97 out of 5 average rating, 151 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

RashaRating, 5 stars6 days ago
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.
Top guest favorite
Guesthouse in South Salem
4.94 out of 5 average rating, 281 reviews

1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt

JamesRating, 5 stars3 weeks ago
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.
Superhost
Apartment in Milford
4.86 out of 5 average rating, 273 reviews

The Farmhouse Estate Apartment

Elly and ScottRating, 5 stars1 week ago
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!
Top guest favorite
Apartment in Ossining
4.96 out of 5 average rating, 425 reviews

Hudson River Peaceful Getaway, Explore from here

ChrisRating, 5 stars1 day ago
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.
Guest favorite
Apartment in Middletown
4.88 out of 5 average rating, 301 reviews

3 bedroom near Wesleyan, downtown

BangheeRating, 5 stars1 month ago
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!
Top guest favorite
Cottage in Redding
4.93 out of 5 average rating, 259 reviews

Cozy Cottage by the pond

MaryEllenRating, 5 stars1 week ago
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

Top guest favorite
Barn in Bethel
4.98 out of 5 average rating, 233 reviews

Escape to a Restored New England Antique Milk Barn

StaceyRating, 5 stars1 week ago
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! ☺️
Guest favorite
Home in Stormville
4.94 out of 5 average rating, 178 reviews

Private Hudson Valley Country Retreat

MarkRating, 5 stars4 months ago
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
Guest favorite
Home in Stony Brook
4.93 out of 5 average rating, 522 reviews

Spacious Studio Apartment- near SBU

JaimeRating, 5 stars1 month ago
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 :)
Top guest favorite
Home in Cheshire
5 out of 5 average rating, 132 reviews

Pool House

MelissaRating, 5 stars3 months ago
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.
Top guest favorite
Home in Monroe
4.97 out of 5 average rating, 200 reviews

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars1 month ago
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!
Guest favorite
Condo in Mount Sinai
5 out of 5 average rating, 33 reviews

1856 Trading House close to water

JulieRating, 5 stars3 months ago
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.
Home in Yorktown Heights
4.89 out of 5 average rating, 9 reviews

* Overlook the Reservoirs Custom Victorian Farmhse

TimothyRating, 5 stars3 months ago
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!
Superhost
Home in Fairfield
4.94 out of 5 average rating, 35 reviews

Newly-Renovated, Private, 4BR Cape w/Pool

PeterRating, 5 stars7 months ago
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

    ﺩ.ﺇ184 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

Destinations to explore