Kid-friendly holiday rentals in Madison

Find and book unique family-friendly rentals on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Madison family-friendly rentals

Kid-friendly house rentals

Guest favourite
Home in Branford
4.97 out of 5 average rating, 34 reviews

Adorable Beach House on LI Sound

JessieRating, 5 stars6 days ago
Such a beautiful place! So much to walk to and had great views of the ocean. Very clean and tidy space with everything you would need! Eileen was very responsive and super friendly. Defiantly coming back!
Top guest favourite
Home in Lyme
4.98 out of 5 average rating, 270 reviews

“The Answer” Your Unique, Tidal, Riverfront Escape

BrianRating, 5 stars5 days ago
It’s feels like pressure to write a review that stands up to ALL the other incredible reviews. I suppose we should stop there because that says it all. But we will add this: Ellie and Tower either wrote the book on hospitality or they read it 100 times. There is no doubt you will get the sense that everything is done with an eye to making you happy and comfortable…. And they do that in Spades. If this place caught your eye… act now… it will capture your heart as well.
Guest favourite
Home in Westbrook
4.96 out of 5 average rating, 26 reviews

Barnacle Bay Beach House

AshlynRating, 5 stars1 day ago
My husband, dog, and I LOVED our stay here- so much that Danielle accommodated for us to stay an additional day! It was the perfect location. Private enough where we felt secluded, but yet right off of a main road with so many great restaurants to walk to! The beach was about a 5 minute walk, and left us with the perfect spot and feeling like we had the beach completely to ourselves the days we were there. We are already talking about going back, and can’t wait to plan our next trip. Thanks so much!
Top guest favourite
Home in Branford
4.95 out of 5 average rating, 111 reviews

Charming home, easy access to everything Branford

KatyRating, 5 stars1 month ago
super nice place. comfortable beds. Great backyard. super responsive and friendly hosts. Will book again!
Superhost
Home in Westbrook
4.79 out of 5 average rating, 125 reviews

The Dragon Fly Garden

DeannaRating, 5 stars3 weeks ago
We had a marvelous stay with our friends and dogs. The location and grounds were perfect for getting to our daytime event and the Dragonfly Garden was serene for relaxing in the evening enjoying tasty delivered dinners. Thanks, Todd. We will definitely stay there again when we are in the area!
Top guest favourite
Home in Haddam
5 out of 5 average rating, 126 reviews

Cozy Comforts!

AlRating, 5 stars5 days ago
We stayed here while attending a friend’s wedding celebration. It was conveniently located for our purposes, right in between each day’s events. It is a quiet area. The space itself was spacious and comfortable and clean. It is a newer place with all you need for a good stay. Helpful and convenient touches included having a few snacks and drinks available which was a big plus with our late arrival.
Guest favourite
Home in Southington
4.95 out of 5 average rating, 116 reviews

Connecticut Chalet - Private Pond, Firepit, Views!

AnthonyRating, 5 stars1 month ago
We were looking to stay somewhere peaceful and relaxing to celebrate a graduation, and this property hit every mark. In a weird way, the photos dont do it justice with how nice the property is and how comfortable it was to stay in. The host was also very responsive and reasonable with our check in / check out. 10/10 will try to come back one day!
Top guest favourite
Home in Milford
4.99 out of 5 average rating, 111 reviews

The ARLO - Walk to Brewery & Restaurants

LaurieRating, 5 stars1 week ago
The ARLO was super cute and very clean. It had ALL the amenities we needed. Outstanding communication with the hosts. Great welcome guide full of info. that answers all your questions. Looking forward to coming back 💕

Family-friendly apartment rentals

Superhost
Flat in East Haddam
4.79 out of 5 average rating, 284 reviews

The Federal Suite at the Wisteria Rest

DanRating, 5 stars1 month ago
Very nice apt and perfect for a quick weekend getaway.
Guest favourite
Flat in Old Lyme
4.89 out of 5 average rating, 198 reviews

Private apartment in historic Old Lyme mansion

BridgetRating, 5 stars2 weeks ago
I can’t say enough good things about our stay at Holly’s place! We were traveling with 2 adults, an 18 year old and significant other and 2 teenagers and the amount of space was perfect! Everyone had room to spread out. The apartment had all the things you love about old homes, but all the updates that make life easier. The homemade banana bread that Holly left for us was such a personal touch and it was delicious. Erica greeted us with a warm welcome even though we arrived well past midnight. My daughter enjoyed reading in the cozy sitting area by the window. It was fun to watch the Hallmark movie that was filmed there. We fast forwarded the cheesy parts and enjoyed seeing the house in the movie. The area is peaceful and quaint. There’s a Dunkin about 5 minutes away, too which made our early mornings a little easier. Highly recommend if you’re traveling with a family!
Guest favourite
Flat in Branford
4.97 out of 5 average rating, 107 reviews

Ridgeview Suite at Stony Creek Depot

EmilyRating, 5 stars1 week ago
Barbara’s place reminded me of the way airbnbs used to be. It felt like home-away-from-home. The accommodations were high quality and clean, and there were even some tasty snacks! We loved our stay. Everything was as pictured. Stony Creek was wonderful, and we look forward to visiting again next year!
Top guest favourite
Flat in Chester
4.98 out of 5 average rating, 167 reviews

Charming Chester Retreat - Cottage

JackieRating, 5 stars1 week ago
Wow!!! This is the nicest airbnb I have ever stayed in. The property is beautiful and peaceful, surrounded by trees with lots of privacy. The cottage itself is immaculate (I’m very particular about cleanliness). The dining area is stunning with skylights and beautiful trees outside and great light! The hosts were also so welcoming and friendly, they included so many nice touches for my baby including a pack and play/travel crib, diaper changing area, and toys! I hope to stay here again every time we come to this area!
Top guest favourite
Flat in New Britain
4.95 out of 5 average rating, 193 reviews

Spacious Cozy Guest Suite

AlbertRating, 5 stars5 days ago
We booked this place to be close the the festival downtown and it was. 1.3 miles or 25 minutes walk. Perfect for us. The Airbnb was clean and spacious. Shower is a little small but ok. King bed is very comfortable. Yummy welcome treats on the table was a nice touch. Keurig pods and maker available for your pleasure. Well lit and very secure. Felt safe at all times. Great place to book if you need to stay in this area.
Guest favourite
Flat in Middletown
4.94 out of 5 average rating, 805 reviews

Quaint 2br apt- 1 block walk to Wesleyan & Main St

AndreaRating, 5 starstoday
Mark’s place was clean and neat. I love that there was a little light and a charging station by the bed. I also loved that there was a full length mirror, which came in handy for getting dressed for my event. Thanks for the use of your space.
Top guest favourite
Flat in Milford
4.98 out of 5 average rating, 104 reviews

The Pond Mill Retreat w/ 2 Bdrms & Pool

JudyRating, 5 stars1 week ago
Dawn and Bob’s place is one of the top Airbnb’s we have stayed in! Top notch in every way. It was spotless, comfortable and had everything we needed. And on top of that Dawn and Bob were the most friendly hosts we have met! I would recommend this Airbnb without reservation and will be back whenever we are back in CT!
Top guest favourite
Flat in Branford
4.99 out of 5 average rating, 109 reviews

Downtown Branford Retreat - Quiet yet Central Apt

JudithRating, 5 stars6 days ago
Andrew‘s apartment in the center of Brantford was very clean and neat. The bathroom was beautiful. All the appliances were new and updated. check-in was easy, It’s in a great location. We loved staying there. Thank you, Andrew.

Family-friendly apartment rentals

Superhost
Apartment in Wooster Square
4.84 out of 5 average rating, 285 reviews

Stunning, Spacious, Spotless. Close to Yale.

TomRating, 5 stars3 weeks ago
Over $500 a night was very high, much higher than west Coast pricing for two bedrooms near a major university. Convenient to Yale but know that poverty has always been evident a few feet from Yale borders and much of the foot traffic consists of the homeless. Also some noise at night from passing traffic. On the plus side there’s an excellent Italian bakery/gelato cafe across the street run by a husband wife team that makes everything they serve.
Top guest favourite
Apartment in Uncasville
4.98 out of 5 average rating, 108 reviews

CASiNO, Spa, Hot Tub, Pool, King bed, sauna

MelindaRating, 5 stars6 days ago
The Villa was exactly as described! Easy communication with owner. A perfect getaway weekend, every amenity we could want or need! Look forward to visiting again in the near future!
Superhost
Apartment in New Britain
4.82 out of 5 average rating, 126 reviews

New Britain "Joy of Small Space" Condo

AdamRating, 5 stars1 week ago
Muna was incredible start to finish with my stay. Helpful, communicative and accommodating. Place was perfectly as described. Genuinely recommend a stay at her place!
Guest favourite
Apartment in Middletown
4.94 out of 5 average rating, 154 reviews

Entire place to yourself Cromwell/Middletown Line

PamRating, 5 stars3 days ago
Will definitely be repeat customers when we come back to CT to see friends and family. The place is exactly as described, spotless and was a home away from home. Elizabeth answered any questions quickly. Thank you for making our first experience with Air Bnb a positive one.
Top guest favourite
Apartment in Uncasville
4.98 out of 5 average rating, 182 reviews

Peaceful Oasis steps from Mohegan Sun

EricRating, 5 stars2 weeks ago
We had a great time and the property was immaculate! The hosts came by with extra towels quickly upon request and it was a holiday. Recommended!
Top guest favourite
Apartment in Uncasville
4.98 out of 5 average rating, 137 reviews

The Vacay Villa

SusanRating, 5 stars3 weeks ago
This is a wonderful property that is close to everything we like to do! Krista is a wonderful host and I’m always excited if her place is available.
Superhost
Apartment in North Fork
4.9 out of 5 average rating, 125 reviews

Seaside Summer Escape –2BR Waterfront Condo w/Pool

DebbieRating, 5 stars1 month ago
We had a great time at Julie’s place. Would love to visit again…perhaps in the Fall. Loved the balcony overlooking the Sound. Julie was very responsive to my questions. She got back to me immediately. I would highly recommend Julie’s home!
Guest favourite
Apartment in North Fork
4.92 out of 5 average rating, 139 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

MorganRating, 5 stars2 weeks ago
We had a great stay! Instructions were clear and the home had everything we needed.

Quick stats about holiday rentals that are kid-friendly in Madison

  • Total rentals

    30 properties

  • Total number of reviews

    1.5K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 properties include access to wifi

Destinations to explore