Kid-friendly holiday rentals in Madison

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Madison

Guests agree: These kid-friendly rentals are highly rated for location, cleanliness and more.

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Guest favourite

Cottage in Guilford

4.96 out of 5 average rating, 158 reviews

Luxury cottage by the sea with hot tub and pool

We built this guest cottage to provide an ultimate luxury experience for people wanting to escape from hectic life!With incredible coastal views, this home is a haven of tranquility. It sits on a special stretch of the Connecticut coast, with spectacular bird and wild life-watching year-round. Enjoy great shopping in Guilford's boutiques around the historic town green. Watch the sun set over the water and relax in the hottub for some night time star gazing year round (pool open June-beg/mid Oct)

22–29 Dec

$1,039 NZD per night

Guest favourite

Cottage in Guilford

4.93 out of 5 average rating, 245 reviews

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

We are sharing our "happy place". Cozy, family-friendly cottage has everything you need to enjoy a lovely vacation in a quintessential New England town. Ideally located between Guilford's famous green, gorgeous harbor and town beach, easily walk everywhere. High-season/weekend rate reflected in general view--check for actual. Recommended for groups of up to 4 (5 if with kids). Second bedroom (king) is open to living area-we provide a folding screen for door area and curtain for “passthrough”.

8–15 Oct

$570 NZD per night

Guest favourite

Apartment in Guilford

4.98 out of 5 average rating, 250 reviews

Guilford Guest House- private studio apartment

Quintessential New England shoreline town. Arrive by Car, Train or by boat and walk from the marina to our guest house. (Inquire) Walk to the Guilford Green, Town Dock, Jacobs Beach along with over a dozen restaurants, pubs, coffee shops, gift & clothing shops. Hiking trails . Please review my extensive guide book of Guilford and the surrounding areas. Walking access to the Shoreline East train to surrounding Local towns or transfer to Metro north and Amtrak to NYC & Boston all without a car.

23–30 May

$331 NZD per night

Guest favourite

Guest suite in Wallingford

5.0 out of 5 average rating, 502 reviews

Wintergreen Gardens Suite @ William Becroft House

LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, pvt. entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station. Coming for a special event? Book an appointment at our salon, Jimmy James Salon. Ask for info.

20–27 Jan

$168 NZD per night

Guest favourite

Yurt in Guilford

4.9 out of 5 average rating, 101 reviews

Hartwoods Yurt

Enjoy a unique, private, wilderness getaway and unwind in a peaceful wooded environment in our 30’ diameter Yurt, which sleeps 4 in North Guilford, CT. This elevated cylindrical dwelling offers solitude and a large deck with comfortable chairs and forest views. Shaded and cool in the summer with air conditioning and fans available. This Yurt provides a wonderful respite from the hectic world. Perfect for nature lovers with a nearby brook and miles of trails for hiking and mountain biking.

17–24 Dec

$438 NZD per night

Guest favourite

Home in Milford

4.98 out of 5 average rating, 153 reviews

Designer Beach Retreat on Exclusive Cedar Beach

Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!

18–25 Nov

$660 NZD per night

Guest favourite

Home in Clinton

4.97 out of 5 average rating, 173 reviews

Waterside Beach Retreat

Beautiful New England period home steps from the beach on the Long Island Sound. Recently renovated from top to bottom with new kitchen and bathrooms, hardwood floors throughout. Idyllic location on quaint & quiet street. Hide away and relax or discover the many local attractions - water sports, fishing, winery, antique stores, scenic walks, premium outlet shopping are all on your doorstep. Ideally located off the I-95 halfway between NYC & Boston, both of which are a train ride away.

23–30 Dec

$838 NZD per night

Guest favourite

Tiny home in Guilford

4.94 out of 5 average rating, 204 reviews

Stay in a Tiny House on a Small Sustainable Farm

Come stay in a tiny house on our sustainable farm! Tucked behind an unassuming neighborhood, feel your cares drop away as you drive down the long gravel driveway and our bucolic 8 acres open in front of you. We have goats, ducks and chickens. Hike, swim, kayak, play with goats, have a picnic or just plain relax. There are so many possibilities. The tiny house has AC/heat, wifi, full kitchen, full bath and a queen sized bed in the loft. Get away from it all here at Waystone Farm.

2–9 Sep

$345 NZD per night

Superhost

Cabin in East Haddam

4.89 out of 5 average rating, 359 reviews

Getaway Machimoodus - NYC/Boston

An easy drive from the city, Getaway is a new way to experience the great outdoors. Nestled across dozens of acres of private woodlands, our modern, tiny cabins have everything you need (comfy bed, bathroom, fresh linens) and nothing you don’t. Featuring a private outdoor area (hello, fire pit), each cabin is designed to help you relax, unwind and disconnect from the everyday. Plus, as part of your stay, you'll receive firewood, a s'mores kit, coffee and bottled water*.

2–9 May

$293 NZD per night

Guest favourite

Apartment in East Haddam

4.89 out of 5 average rating, 106 reviews

Penny Corner Airbnb

My place is located up the hill from Good Speed Opera House. The Opera House is on the same side of the river as my place. The folklore is that vacationers used to pay a penny to have their belongings transported by ox and wagon from the port at the river to this corner. A two family home built in 1884. The space is a ground level 1 bedroom apartment with private entrance. There is no TV in the unit, WIFI is available for your devices.

11–18 Feb

$198 NZD per night

Guest favourite

Guesthouse in Guilford

4.99 out of 5 average rating, 454 reviews

Get Back to Nature at a Modern Wood Clad Getaway

SPRING BIRDS HAVE ARRIVED. Spring is here!!. Beautiful days and nights. Hike on the trails. Bike along the ocean. Cardinals, blue jays, bluebirds, gold finches and more. Great places to shop and eat or just relax in our cozy guest house. Enjoy! We want you to have a relaxing stay with us, free from worry. We are located in a private area, away from public.

26 Nov – 3 Dec

$562 NZD per night

Guest favourite

Guest suite in New Haven

4.99 out of 5 average rating, 157 reviews

Cozy cottage in historic neighborhood

Housed in a 100-year-old building nestled between the Victorian houses in New Haven's historic City Point neighborhood, once the center of New England's oyster trade, our cottage is a two-block walk from the marina (and its award-winning restaurant), a 10 minute-drive from the West Haven beaches and a few minutes' drive to Yale.

24 Jun – 1 Jul

$296 NZD per night