Family-friendly vacation rentals in Fairfield

Find and book unique family-friendly homes on Airbnb

0 of 0 items showing
1 of 3 pages

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 stars34 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, 19 reviews

Chic Beach House: Waterfront, Vineyards, Hot Tub

SamRating, 5 stars4 days 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!
Guest favourite
Villa in Hopewell Junction
4.96 out of 5 average rating, 290 reviews

The Mission House Sanctuary

MiriamRating, 5 stars5 months ago
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.
Superhost
Home in Shippan Point
4.94 out of 5 average rating, 114 reviews

OCEAN COAST LUXURY BEACH HOUSE/45 min to NYC

JonathanRating, 5 stars7 months ago
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 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
Townhouse in Greenwich
4.94 out of 5 average rating, 70 reviews

Quaint duplex + pvt yard. Walk to town & beach!

SamanthaRating, 5 stars1 month ago
I had an amazing stay at this Airbnb! Henri was incredibly responsive and made sure all of my questions were answered promptly, which made the whole process seamless and stress-free. The home itself was spotless, well-maintained, and had everything we needed for a comfortable stay. It was spacious and thoughtfully stocked with all the essentials, from kitchen items to fresh linens. I felt right at home from the moment I arrived. Highly recommend this place if you're looking for a welcoming, comfortable, and well-equipped spot to stay!
Guest favourite
Cottage in North Fork
4.97 out of 5 average rating, 150 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

JenniferRating, 5 stars4 months ago
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.
Top guest favourite
Guesthouse in South Salem
4.94 out of 5 average rating, 280 reviews

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

JamesRating, 5 stars3 days 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, 271 reviews

The Farmhouse Estate Apartment

TravonRating, 5 stars1 week ago
It was Very Great, calm, quiet. In our stay, the guests upstairs were very friendly, even during after hours. The vast land in the backyard was very enlightening , came across a couple of the friendly and nosy neighbors (The Deer😂 🦌). Overall it was very clean & i loved every minute of it.
Guest favourite
Apartment in Guilford
5 out of 5 average rating, 6 reviews

Lakefront Country Oasis

SergioRating, 5 stars9 months ago
Margie’s place is an amazing hidden gem. The inside is very clean and comfortable. The outside is an experience of its own. The lake will drop your blood pressure immediately. Gorgeous surroundings. The dogs are friendly and lovable. We will be back! 👍🏼
Cottage in Port Jefferson Station
4.8 out of 5 average rating, 448 reviews

The Red Cottage Circa 1936

StephenRating, 5 stars2 weeks ago
Jennifer's place was adorable, so many nice personal touches on the place. Exactly as described and the fish tank was a nice touch, very relaxing. Would highly recommend and will stay again next time im in town. Thank you for everything.
Top guest favourite
Cottage in Redding
4.93 out of 5 average rating, 257 reviews

Cozy Cottage by the pond

LauraRating, 5 stars4 months ago
Perfect stay in the coziest cottage! Rose & Jamie were amazing and super helpful and made us feel right at home.
Superhost
Home in Woodmont
4.91 out of 5 average rating, 35 reviews

Beachfront, Dog Friendly

AslynnRating, 5 stars4 months ago
Thank you for a wonderful stay and accommodating an extra night.

Family-friendly home rentals with a pool

Top guest favourite
Apartment in Redding
5 out of 5 average rating, 17 reviews

Poolside apartment with private tennis court.

MauroofRating, 5 stars10 months ago
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!
Top guest favourite
Barn in Bethel
4.98 out of 5 average rating, 231 reviews

Escape to a Restored New England Antique Milk Barn

AbeRating, 5 stars1 week ago
When my plumbing went rogue and turned my floor into a squishy disaster zone, I needed a place to crash that wasn’t half underwater. Enter Sally’s place—a true oasis in my time of crisis. First off, this place is so nice that I briefly wondered if my house was even worth saving. It’s cozy, beautifully decorated, and so clean. The bedroom and bathroom are upstairs, making me feel like I was living the high life—literally. The bed? Like sleeping on a cloud. The view? So peaceful I considered writing poetry. Bottom line: If you need a place to stay, stop scrolling. Just book it. But be warned—you may never want to leave.
Guest favourite
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
Top guest favourite
Home in Cheshire
5 out of 5 average rating, 131 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 favourite
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 favourite
Cottage in Redding
4.96 out of 5 average rating, 23 reviews

Guesthouse & private pool, historic 24-acre estate

IanRating, 5 stars7 months ago
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!
Guest favourite
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.
Superhost
Home in Fairfield
4.94 out of 5 average rating, 35 reviews

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

PeterRating, 5 stars6 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

    $70 CAD before taxes and fees

  • Total number of reviews

    4.2K reviews

  • Pet-friendly rentals

    90 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