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

Top guest favorite
Home in North Fork
4.97 out of 5 average rating, 205 reviews

Private Oasis W/Stunning Vinyard and Pool Views

RebeccaRating, 5 stars3 weeks ago
We loved staying at this home - it was the perfect place for our group of ten. The outdoor space was definitely the highlight, with the pool & spa being our favorite part of the trip. The only thing to note is that we weren’t supplied quite enough toilet paper or paper towels, though I did not reach out for more - It was the last evening when we ran out and we were leaving early the next morning. The trash requirements were a surprise after booking, but going to the transfer station was easy enough, and it is listed on the house rules. Overall, an excellent stay and would absolutely return!
Top guest favorite
Home in Wading River
4.96 out of 5 average rating, 503 reviews

Your Zen Retreat

LisaRating, 5 stars3 weeks ago
This was the most beautiful house in a private area in Wading River. It offers peace and tranquility and lives up to its name of Zen Retreat. It was exactly what we were seeking. Conveniently located near parks, farms and wineries I would definitely go back to Brian’s AirBNB. He was an excellent host and very responsive to our needs. Thank you Brian.
Superhost
Home in Shippan Point
4.94 out of 5 average rating, 116 reviews

OCEAN COAST LUXURY BEACH HOUSE/45 min to NYC

DebraRating, 5 stars1 month 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!
Guest favorite
Home in Cold Spring
4.95 out of 5 average rating, 323 reviews

Hilltop Hideaway Forest Villa on 13 acres!

JillRating, 5 stars2 weeks ago
Paula was an exceptional host! She was always quick to respond and answered my many questions, before and during our stay. The house was fantastic for entertaining. It’s spacious and we loved the art! We would have loved to enjoy the beautiful decks, but it rained during most of our visit. We made a fire instead! The house has Sonas and we loved having music. The large windows are great and so were all the views. It made me feel like I was in a treehouse! I would highly recommend this Airbnb and host.
Guest favorite
Guesthouse in Beacon
4.94 out of 5 average rating, 399 reviews

Cozy Mountainside Suite - Minutes from Beacon

TinaRating, 5 stars1 month ago
My boyfriend and I booked last minute trip! That turned out magical ! The view was priceless, the hot tub was large and had message features, hammock was great. Suite is adorable and very clean. You’re literally on top of a mountain with no neighbors and surrounded by nature. Very private ! We caught an amazing view day and night on a clear sunny day and then a lightning storm in the mist! We missed our farm friends as soon as we left. Accurate listing ! Highly recommend 4wheel drive !
Guest favorite
Home in Cold Spring
4.91 out of 5 average rating, 258 reviews

1834 Farm House

MadelineRating, 5 stars1 month ago
We keep coming back to stay here because the house is so cool and has everything you could need! A great getaway outside of nyc anytime and we always recommend to others.
Guest favorite
Home in Englewood
4.94 out of 5 average rating, 156 reviews

Englewood NJ Country Carriage House (15 min NYC)

LipingRating, 5 stars3 weeks ago
We absolutely loved the living environment there. It was incredibly quiet, providing the perfect peaceful retreat. The landlord went above and beyond by sending us over 20 detailed instructions in advance, explaining how to use every facility in the apartment. From start to finish, everything was meticulously arranged. We were all extremely satisfied with this stay
Guest favorite
Home in Westhampton Beach
4.93 out of 5 average rating, 149 reviews

Hampton's Haven

DavidRating, 5 stars1 week ago
Esther is hands down one of the finest hosts we have had, and her house is beautiful and was spotless upon arrival and everything worked from pool to hot tub to grill etc... Area is very quiet. great place to relax with a mature group of friends or with your family. Esther was always responsive. Me and my crew have been renting houses for over three decades (Way before AirBnB). Esther is at the top of the list hands down. Thank you for everything. Will 1000% be back. ANd you shuld rent there too. You will not be disappointed.

Family- and pet-friendly home rentals

Superhost
Home in Huntington
4.85 out of 5 average rating, 294 reviews

Nautical Farm House on Working Farm with Animals

AnneRating, 5 stars1 month ago
Love staying here! It was perfect for our family. Had two toddlers and a baby and it worked out so great for us after renting some baby equipment (pack n play and high chair) from a third party. The kids loved the animals and the ducks and chickens that would greet us in the yard. a nice patio we had a couple dinners and snacks at. A homey, stylish and perfect place for us. Needed to keep the doors locked even if just going to the cafe, there were some people who were exploring our yard even though the signs said it was private. Someone was parked in our designated spot just once, otherwise was very nice to have a parking spot. The remote for the tv was lost the first few days till the maid graciously came by and helped us find it tucked in the couch. We could not stop talking about how perfect the place worked out for us. It was so charming and such a great place for the kids to enjoy. Would definitely recommend and stay again sometime!
Superhost
Apartment in East Rock
4.9 out of 5 average rating, 213 reviews

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

kimRating, 5 stars1 month ago
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.
Guest favorite
Cottage in North Fork
4.97 out of 5 average rating, 154 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

BrettRating, 5 stars4 days ago
Look no further! The Beach Cottage is beautiful, immaculate, private, and all things one would hope a vacation getaway would entail. This location feels “off the grid” albeit close to modern amenities/stores. Hope to be back soon!
Guest favorite
Loft in Getty Square
4.94 out of 5 average rating, 341 reviews

Blacksmith Bldg Guesthouse Upscale in downtown.

MichaelRating, 5 stars3 weeks ago
We had a terrific experience with Robert's apartment. The hosts were flexible, informative, and responsive. The unit was extremely clean and well appointed with little touches that we appreciated. It is in a quiet part of downtown with walkable access to the waterfront, good coffee, and excellent restaurants. If you have a reason to be in the Yonkers region I couldn't recommend it highly enough.
Superhost
Cabin in New Milford
4.84 out of 5 average rating, 136 reviews

A-Frame Cottage off Candlewood Lake

PaulRating, 5 stars1 month ago
Emily and Carol were wonderful hosts. They were responsive to our questions and provided great recommendations. Sitting on the balcony with the view of the trees and the lake beyond was tranquil. The living area is cozily furnished and both the fireplace and tv were easy to use. The nearby community beach was fun to visit and an added benefit of the stay. Great location with plenty of good food and small town charm!
Top guest favorite
Farm stay in Fort Montgomery
4.98 out of 5 average rating, 194 reviews

Secluded overlook cottage near West Point

Alec & LauraRating, 5 stars1 month ago
We loved staying here, and our son loved visiting the horses, and the chickens in the barn. And we saw wild turkeys and deer roaming the property. And it was great to see the horses run on our way out! There are also lots of little streams and tiny waterfalls we enjoyed checking out. And the farm fresh eggs were a lovely and much appreciate bonus!
Guest favorite
Cottage in Guilford
4.93 out of 5 average rating, 272 reviews

Charm + location. Walk to beach, town, & harbor.

KathleenRating, 5 stars1 week ago
It was so comfortable and peaceful. We had a great time exploring nearby beaches and hikes. We would definitely stay there again.
Guest favorite
Apartment in Carmel-by-the-Sea
4.87 out of 5 average rating, 298 reviews

Private space, with yard

EmilyRating, 5 stars2 weeks ago
We had a great stay here as we explored nearby things (the Chuang Yen Monastery was delightful!) and visited some favorite spots. The weather was a little dreary when we were there, otherwise we would have made good use of the beautiful outdoor space. It was the perfect place for us to relax after our adventures every day—very quiet, very comfortable, clearly-written instructions for everything. We would be very happy to return!

Family-friendly home rentals with a pool

Superhost
Apartment in Huntington
4.64 out of 5 average rating, 198 reviews

"House of Tranquility!" Private Apt., Great Area!

JasonRating, 5 stars6 days ago
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.
Guest favorite
Home in Stormville
4.94 out of 5 average rating, 179 reviews

Private Hudson Valley Country Retreat

MarkRating, 5 stars6 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
Superhost
Home in Hampton Bays
4.95 out of 5 average rating, 129 reviews

Peaceful Retreat in Immaculate Architect’s House

TheanoRating, 5 stars1 month ago
We had an amazing stay at Michael’s Airbnb this past weekend! The space was exactly as described—clean, cozy, and well-equipped with everything we needed. Michael was a fantastic host: super responsive, thoughtful, and made us feel completely at home. The location was perfect for a relaxing getaway, and the setting was even more beautiful in person. Would absolutely stay here again—thank you for a wonderful experience, Michael!
Guest favorite
Home in Stony Brook
4.93 out of 5 average rating, 535 reviews

Spacious Studio Apartment- near SBU

ElizabethRating, 5 stars1 week ago
Gabby’s apartment is exactly as described. It is in a great location. Very close to Stoney Brook Village. We enjoyed walking to get our morning coffee. The apartment was very well stocked and spotless. Gabby thought of everything we could have possibly needed. We hope to be back next year!
Top guest favorite
Home in Cheshire
5 out of 5 average rating, 135 reviews

Pool House

CindyRating, 5 stars3 weeks ago
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!
Guest favorite
Apartment in Glastonbury
4.89 out of 5 average rating, 438 reviews

Quiet 2 bed room apt w/ private entrance.

JoshRating, 5 stars3 weeks ago
Alice’s place was great! We’ll be back again for sure.
Guest favorite
Home in Fairfield
4.94 out of 5 average rating, 37 reviews

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

KerriRating, 5 stars3 weeks ago
This is the second time we stayed at this house. The owner is super nice and very accommodating. The house was great! Clean, beautiful yard, close to campus. We would highly recommend!
Guest favorite
Home in Cold Spring
4.95 out of 5 average rating, 170 reviews

Cozy, Modern Retreat in the Woods of Cold Spring

AndyRating, 5 stars3 weeks ago
It was comfortable, very roomy, and cozy. There was good shared space and good privacy. The grounds were lovely, there was a great pool, and it was very convenient to so many good things to do in the area. It's one of our favorite rentals to date!

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

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