Family-friendly vacation rentals in Fairfield

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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 reviews

Luxury Penthouse Minutes to Yale

ZachRating, 5 stars1 month ago
Good location host is very communicative
Superhost

Home in North Fork

4.94 out of 5 average rating, 17 reviews

Chic Beach House: Waterfront, Vineyards, Hot Tub

OzanaRating, 5 stars6 months ago
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!
Guest favorite

Villa in Hopewell Junction

4.96 out of 5 average rating, 289 reviews

The Mission House Sanctuary

MiriamRating, 5 stars1 month 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.

Home in Stormville

5 out of 5 average rating, 11 reviews

2 MasterSuites Heated SaltWater Pool+HotTub&More

DeborahRating, 5 stars40 months ago
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!
Guest favorite

Home in Shippan Point

4.94 out of 5 average rating, 114 reviews

OCEAN COAST LUXURY BEACH HOUSE/45 min to NYC

JonathanRating, 5 stars4 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 Branford

4.88 out of 5 average rating, 68 reviews

Amazing Waterfront Home, Private Beach & Hot Tub

PeterRating, 5 stars2 weeks ago
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.
Guest favorite

Home in Putnam Valley

4.99 out of 5 average rating, 74 reviews

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

AnthonyRating, 5 stars1 week ago
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 reviews

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

PatrickRating, 5 stars6 months ago
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

Guest favorite

Apartment in East Rock

4.9 out of 5 average rating, 208 reviews

3 RM Apt. w/kit. in historic house

MaeveRating, 5 stars2 months ago
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 :)
Guest favorite

Cottage in Middlefield

4.92 out of 5 average rating, 244 reviews

Lake Beseck cottage

KathyRating, 5 stars2 months ago
I love staying at Elisabeth’s place! It has become my “home away from home”. Cozy, comfy and just perfect!
Guest favorite

Cottage in North Fork

4.97 out of 5 average rating, 150 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

JenniferRating, 5 stars3 weeks 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.
Guest favorite

Guesthouse in South Salem

4.94 out of 5 average rating, 267 reviews

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

SandyRating, 5 stars2 weeks ago
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!
Guest favorite

Apartment in Milford

4.87 out of 5 average rating, 262 reviews

The Farmhouse Estate Apartment

AmandaRating, 5 stars1 month ago
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!
Superhost

Cottage in Port Jefferson Station

4.8 out of 5 average rating, 433 reviews

The Red Cottage Circa 1936

JoeRating, 5 stars1 month ago
Jennifer was a gracious host. We had everything we needed for a perfect stay. Highly recommend! Thank you for hosting us! Joe and crew
Guest favorite

Apartment in Ossining

4.95 out of 5 average rating, 392 reviews

Hudson River Peaceful Getaway, Explore from here

StevenRating, 5 stars1 week ago
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.
Guest favorite

Cottage in Redding

4.93 out of 5 average rating, 257 reviews

Cozy Cottage by the pond

LauraRating, 5 stars4 weeks ago
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

Guest favorite

Apartment in Redding

5 out of 5 average rating, 17 reviews

Poolside apartment with private tennis court.

MauroofRating, 5 stars6 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!
Guest favorite

Barn in Bethel

4.98 out of 5 average rating, 223 reviews

Escape to a Restored New England Antique Milk Barn

CullenRating, 5 stars1 month ago
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!
Guest favorite

Home in Stormville

4.94 out of 5 average rating, 178 reviews

Private Hudson Valley Country Retreat

MarkRating, 5 stars3 weeks 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, 512 reviews

Spacious Studio Apartment- near SBU

NickRating, 5 stars3 weeks ago
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!
Guest favorite

Home in Cheshire

5 out of 5 average rating, 130 reviews

Pool House

DavidRating, 5 stars2 weeks ago
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.
Guest favorite

Home in Monroe

4.96 out of 5 average rating, 199 reviews

Garden Level Suite with Beautiful Pool

CarolRating, 5 stars2 months ago
This was our third stay at Marybeth's, everything was great, as usual. The unit is spacious, clean, and very conveniently located.
Guest favorite

Cottage in Redding

4.95 out of 5 average rating, 22 reviews

Guesthouse & private pool, historic 24-acre estate

IanRating, 5 stars3 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!

Home in Yorktown Heights

4.88 out of 5 average rating, 8 reviews

Holiday Escape to Victorian Farmhouse Getaway

AllieRating, 5 stars1 month ago
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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