Kid-friendly vacation rentals in Fairfield County

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Popular amenities for Fairfield County kid-friendly rentals

Kid-friendly house rentals

Guest favourite
Home in Woodbury
4.94 out of 5 average rating, 18 reviews

2 homes in one (in-law design) w/salt water pool

ChristineRating, 5 stars7 months ago
Julie is an outstanding host! This house is perfect for any getaway. It was clean, spacious, well equipped, comfortable, and STUNNING outdoor area with a gorgeous pool. This is 3 FULL baths and 1/2 bath!! Two kitchens! Two family rooms! You had space! It made you want to relax! The kitchen was well stocked with any utensil or appliance you would need. It was private. You could really escape and get away. Woodbury and the surrounding towns were jampacked with things to do. There were many places to choose from to eat. Such a variety from steak, seafood, pizza, and American fare pubs and other specialty restaurants. Lots of variety/antique shops, flea market, wine/liquor stores, convenience stores. Just a short drive into Southbury you find more shops, antiques, restaurants, bigger, grocery store, etc. We also drove to a few other neighboring towns. All under 45 minutes. Friendly people! We had a wonderful time! Price is fabulous, house/outdoor area is A+ value! Thank you Julie!!
Superhost
Home in Milford
4.84 out of 5 average rating, 55 reviews

Charming 2BR Home | Fast Wi-Fi & Outdoor Space

LindaRating, 5 stars4 months ago
Ritestay was a great place. We didn’t spend much time there because we were there to see our daughter. Would be perfect in the summer!!
Top guest favourite
Home in Pawling
5 out of 5 average rating, 224 reviews

Hobbit House of Pawling

LauraRating, 5 stars5 days ago
It’s hard to pick just a few good things to say about this lovely home. The location was perfect for the activities we had planned, however, if we had enough time to just stay at the home, we would have been perfectly happy. Everything exceeded our expectations. The home was very clean, the beds were comfortable. The hot tub and the propane fire pit right next to it, made for a couple of wonderful star filled nights for our small group. There were so many cool things to look at in and around the house, I think we will need to come back to see it all. Can’t wait!
Guest favourite
Home in Southbury
4.9 out of 5 average rating, 21 reviews

Cozy Family and Pet friendly 3 br Home

JennaRating, 5 stars5 months ago
We stayed at Ryan's place while visiting family in the area over the holiday weekend. The place was comfortable and clean and the bonus of being able to bring our pups was the best part. The dog park down the road was amazing and the locals were very friendly. The location was great, very convenient to shops, grocery store, gas etc. Overall we had a great time. Thanks again, Ryan!
Guest favourite
Home in Milford
4.91 out of 5 average rating, 43 reviews

The Seashell House

FaithRating, 5 stars8 months ago
This place was perfect! We were pleasantly surprised by all there was to do in the area nearby and the house came stocked with everything we could’ve needed!
Top guest favourite
Home in Stamford
4.98 out of 5 average rating, 232 reviews

Bright Stylish Chic 4BR 4BA Home

ShefaliRating, 5 stars1 month ago
We had a wonderful time at Deirdre’s place which was a last minute booking. She was very responsive and we felt so much at home, with everything we needed to keep our family of 5 safe and occupied. We especially loved the playroom and books for all ages. The backyard tire swing and bird watching was a hit with my bigger kids too. There was lots of space to spread out if we had come with more family as well. Great stay- thank you again, Deirdre!
Guest favourite
Home in Milford
5 out of 5 average rating, 10 reviews

Huge Family House w/Waterviews

SheilaRating, 5 stars2 months ago
The neighborhood was beautiful. We walked out to an island that was only accessible at low tide. Great shared spaces with fun rooms and lovely bedrooms.
Guest favourite
Home in Milford
5 out of 5 average rating, 6 reviews

Big House On Maddox

DianeRating, 5 stars7 months ago
We stayed here in the entire home for a wedding weekend. Both units were fabulous and Cole was very responsive when we had an issue with the key pad. The bride

Family-friendly apartment rentals

Guest favourite
Apartment in Milford
4.89 out of 5 average rating, 233 reviews

Renovated Apartment in a Historic Farmhouse Estate

TiffanyRating, 5 stars2 weeks ago
Thankful for the accommodations by this wonderful host. Our stay was perfect super greatful to have the opportunity to stay here it was truly great. Home has everything a guest would need. Very quiet & safe neighborhood family friend. Very responsive host as well!!
Guest favourite
Apartment in Milford
4.95 out of 5 average rating, 107 reviews

Downtown, Private balcony, 1gb fiber Wi-Fi

AshleyRating, 5 stars1 month ago
This home was so nice to stay in, it was perfect for my fiancé & I and our frenchie who enjoyed running outside in the front yard! My favorite part definitely had to be the king size bed!! Even though we both work from home, it was absolutely hard to get out of bed every morning lol. The area was just right, quiet & peaceful. Walkable too! Overall, this was the perfect place to stay until we made our way to downtown Stamford to move into our new apartment! We both felt well rested staying here :) ❤️
Guest favourite
Apartment in Stamford
4.94 out of 5 average rating, 109 reviews

The Hillside Crib | 1 Bedroom Apt | Near Downtown

ClaudiaRating, 5 stars4 months ago
The apartment was well maintained, beautifully decorated and clean. Apartment was exactly as described with so many personal touches. My husband and I were so happy with our stay, such a homey feel. Dagmara also gave excellent check in instructions and always quickly responded. I would definitely stay again.
Guest favourite
Apartment in Westport
4.89 out of 5 average rating, 219 reviews

Spacious Westport Apt surrounded by nature

NancyRating, 5 stars1 week ago
My family stayed at Johanna's place for one night and everything was perfect. The check in process was easy, the beds were comfortable, and the location was convenient. It's also worth noting that the water pressure in the shower was fantastic. Overall would definitely recommend and stay again!
Superhost
Apartment in Stamford
4.77 out of 5 average rating, 199 reviews

Downtown "Blue Nest" apartment

AnneRating, 5 stars1 month ago
We stayed for one month. It was a pleasant stay. No issues. Everything was as advertised -- no surprises. Would stay again.
Top guest favourite
Apartment in Fairfield
4.97 out of 5 average rating, 119 reviews

Sunny Fairfield Studio Apartment

LisaRating, 5 stars1 week ago
Clean, quiet and comfortable. We found this apartment to be an outstanding choice for a long weekend after an event at Fairfield University. Everything was so clean and tastefully decorated. The carriage house is located back off the road, making it a quiet and peaceful place to take a break. Having our car parked inside under our apartment was wonderful as we could safely leave items in the car without worry and have easy access to the car at night and during some rain. Comfortable and quality bedding, soft towels and good shower/soap products. Great communication! If I ever return to the area this will be my first choice! Thanks for the great stay!
Guest favourite
Apartment in Brewster
4.88 out of 5 average rating, 104 reviews

The Hideaway

MelodyRating, 5 stars2 weeks ago
Renee’s place was a nice and cozy getaway from the city, and surprisingly fit 5 people + 2 cats very comfortably! She was also very quick to respond to any questions I had, we had a great time!
Guest favourite
Apartment in Middlebury
4.92 out of 5 average rating, 119 reviews

Cozy Apartment with Water View of Brook

JulieRating, 5 stars1 week ago
Our stay was extremely quiet until the upstairs neighbors returned. We don't have kids or pets so we're very used to quiet. Getting used to hearing upstairs neighbors took getting used to for me. The place was chock full of supplies, coffee, Scrabble and welcoming decor. The bed was outstandingly comfortable. The bathroom was modern and creative! The outdoor patio, activities and view of the creek were impressive. This is definitely on our "to return to" list.

Family-friendly condo rentals

Superhost
Condo in Norwalk
5 out of 5 average rating, 3 reviews

Hip, central 2-story loft w Gym and parking

NarenRating, 5 stars7 months ago
Great location and lovely place. Highly recommend to anyone looking to book this place!
Superhost
Condo in Stamford
4.65 out of 5 average rating, 23 reviews

Clean 1 BD apt with Free Wi-Fi and parking

ConnorRating, 5 stars8 months ago
My friend and I stayed for a short trip at Maria's location and it was exactly what we needed, a place to stay for our trip that was well kept, had amenities, and fresh linen available. Parking spot was small, but is to be expected in an attached parking garage.
Superhost
Condo in Fairfield
4.83 out of 5 average rating, 139 reviews

Cozy Condo by Fairfield U/SHU | Patio | Wshr/Dryr

RobertRating, 5 stars3 weeks ago
This was our second stay at Dariel’s place. It is perfect for our family and I always check to see if it is available when we are visiting the area. It is spacious yet cozy, and well-appointed. It is easy to get to, and central to both sides of town.
Condo in Stamford
5 out of 5 average rating, 6 reviews

Quiet, Lovely Condo Downtown with Parking

EmilyRating, 5 stars51 months ago
Marcela was a fabulous host! She is very thoughtful and we had everything we needed. She also responds very quickly. The place was very clean and efficiently organized. It is a true gem. We would definitely stay again! Thank you Marcela!!!!
Guest favourite
Condo in Stamford
4.89 out of 5 average rating, 79 reviews

Downtown gem w/ parking, Wi-Fi+!

VadimRating, 5 stars1 week ago
Great stay! The apartment is spacious, clean, and has everything you need for a comfortable visit. The nearby park is quiet and lovely — perfect for a walk. Highly recommend!
Condo in Greenwich
4.92 out of 5 average rating, 12 reviews

NEW Amazing 2 bd Condo Doorman w/parking GREENWICH

LawrenceRating, 5 stars10 months ago
Our stay was flawless and pleasurable. The rooms were sleek, spotless and very quiet. All had independent temp controls and TV. The kitchen was airy and modern with stainless Viking appliances. All consumables, like coffee filters, were in ample supply. Beds were soft but supportive, with comfortable pillows sheets and quilts. On top of that, the location in the center of Greenwich at the heart of Greenwich Ave. was marvelous. Every evening we could wander down and explore the upscale shopping opportunities, then pick from dozens of excellent, interesting restaurants. Overall an excellent experience and highly worth it.
Top guest favourite
Condo in Stamford
4.86 out of 5 average rating, 64 reviews

Cozy private furnished apartment

HarryRating, 5 stars4 months ago
it was a great stay house was homey nice and clean quiet perfect for a weekend getaway or Any getaway easy to commute with lots of things to do in the area and downtown was festive for the time of year I will deff recommend this place
Guest favourite
Condo in Stamford
4.91 out of 5 average rating, 11 reviews

Downtown Modern Condo!

PaulRating, 5 stars1 month ago
Park out front and unload. Elevators to the right. Parking remote control by the TV (old rectangular box). Turn right out of the circle and take the first right. Go to the double aluminum garage doors to the right. Parking space is on 4th level and fits large SUV's. You don't need the remote to leave. Hope this helps.

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