Kid-friendly holiday rentals in Massachusetts

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Massachusetts

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

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Guest favourite

Farm stay in Southbridge

4.89 out of 5 average rating, 316 reviews

Scandanavian Wigwam with Sauna and Forest Baths

Deep sleeps await in our off grid forest Wigam. With everything you need, and nothing you do not, this exceptional retreat boasts a Danish Morso wood stove, fire pit, private forest baths, Finnish sauna, HUGE windows overlooking a wildlife trail and Peepers Owls and Coyote song. From photo shoots to wedding proposals - this is a special place to care for yourself and your family. We are on farm - but out of sight. Bring your kids, dogs, friends, guitar, or just a good book and settle in!

Guest favourite

Chalet in Otis

4.95 out of 5 average rating, 382 reviews

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Guest favourite

Cottage in Petersham

4.99 out of 5 average rating, 179 reviews

Cider House Cottage

Antique guest cottage on a country farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub.

Guest favourite

Guesthouse in Northampton

5 out of 5 average rating, 320 reviews

Mill River Cottage (pet friendly!)

Welcome to our peaceful and unique urban farm cottage. We are located in historic Florence, Massachusetts (a part of Northampton). While our place is no longer a working farm, the cottage was created many years ago to support the main dwelling. It has been modernized to offer every comfort while maintaining its cozy aesthetic. Free parking & lighted access to the cottage. The cottage is a private space where you can come and go as you please. Relax and unwind or head out to explore the area!

Guest favourite

Treehouse in Tyringham

5 out of 5 average rating, 269 reviews

Gingerbread House Tower in the Berkshire Hills

Escape to this newly renovated, off-beat retreat for a magical stay. Part of Tyringham’s Gingerbread House located on the Santarella Estate in the Berkshires, Western Mass. This one-of-a-kind loft with tower bedchamber offers guests a fairytale experience. The open concept living space filled with plants brings the outdoors inside and offers ample room to relax. If looking for activity, guests can spend the day on the grounds, walking nearby trails, or exploring the many nearby Berkshire towns.

Guest favourite

Tiny home in Wellfleet

4.98 out of 5 average rating, 285 reviews

Writer's Cabin in Woods near Wellfleet Bay

Our unique, creative and magical "Writer's Cabin" tiny house is a guest favorite! You'll be tucked in the woods with the views of a treehouse, and just minutes' drive or bike ride to Wellfleet's beaches, ponds & walking trails. Wellfleet's quaint town center and harbor are just a 10-15 minutes walk down the road. Note: the cabin has a private, wooden Nordic shower w/ hot water built onto the outside of the cabin. Our guests love this unique experience! The toilet is standard flushing & indoors.

Guest favourite

Guesthouse in Scituate

4.93 out of 5 average rating, 100 reviews

Serenity House

Take a deep breath while relaxing on this 1+ acre wooded estate surrounded by the Hubbell Woodland Preserve and the Hatherly Golf Course across the street. Walk along seaside estates that greet you on your way to swim at Minot Beach which is a short walk away. Ride your bike to Cohasset Harbor while taking in the view of the fishermen catching lobsters and have dinner at the local restaurants. Listen to the waves and smell the salty ocean air and relax and sleep peacefully at Serenity House!

Guest favourite

Loft in Greenfield

4.97 out of 5 average rating, 98 reviews

Treehouse Retreat

This loft apartment is on the 3rd and 4th floors of a Victorian mansion. It boasts a dozen skylights and cathedral ceilings, making you feel like you're up in the trees. A jacuzzi tub, full kitchen, and large work tables make this an ideal spot for a relaxing getaway or artist's retreat. Located a couple of blocks from downtown Greenfield. Easy walk to great restaurants, cinema, shops, train station, farmers' market and co-op. 2nd bedroom with king bed and ensuite bath available for fee.

Guest favourite

Rental unit in Falmouth

4.98 out of 5 average rating, 185 reviews

Modern Luxury Apt. | 7 min from Commons

This luxury 1Br + 1bth apartment is the perfect getaway. - 650 square feet, newly renovated - 15 Minutes from Old Silver Beach, South Cape Beach, and Falmouth Heights beaches - Steps from 1,700 acres of walking trails (Crane Wildlife) - 7 minutes to Mashpee Commons (shops and restaurants) - 15 minutes to Main Street Falmouth - 13 minutes to Ferry for Marthas Vineyard - 85” smart TV - 5 minutes to Shining Sea Bike Trail - Coffee/Espresso Machine - 2 minutes from Paul Harney Golf Course

Superhost

Cottage in Fairhaven

4.83 out of 5 average rating, 207 reviews

Cottage by the Bay

Cottage in Fairhaven, perfect for a vacation for a small family, a romantic getaway or a home away from home if you are in the area for business. Enjoy all a vacation has to offer. During warmer weather, walk to the public beach and boat ramp - swim, sun, boat. Spend evenings by the outdoor fireplace. When it is cold out side, enjoy parks, museums, arts and cultural events, with evenings spent enjoying hot chocolate in front of the gas stove as the fire blazes providing a cozy warmth.

Guest favourite

Cottage in Sandwich

4.9 out of 5 average rating, 178 reviews

Blue Anchor Cottage - private hot tub getaway!

This newly renovated cottage is an amenity-filled launching point to explore all of Cape Cod! Just 0.4miles to the beach and with our own hot tub you’ll be able to fully enjoy the Cape's most historic town. Some of our favorites nearby: 2min- your local coffee shop 2min- great fish tacos + bar 2min- nice conservation area hike 2min- local convenience store 7min- downtown Sandwich 7min- golf course 9min- Sandwich Boardwalk 10min- Heritage Museums & Gardens 22min- Cape Cod Rail Trail

Guest favourite

Cottage in Orange

4.93 out of 5 average rating, 159 reviews

The Lake Cottage: A Sweetwater Stay

Welcome to Mattawa Cove! Originally built as an Ice Fisherman's shack, this tiny house is unapologetically elegant and understated. The private dock can be viewed from the wall of windows in the open living space. Walk to the shore, sit with your feet in the water, swim, fish, or kayak. It’s the ultimate, all-year romantic getaway. With excellent Wi-Fi, you can stay as connected as you'd like to the outside world. 1.5 hours from Boston or Providence. 3.5 hours to NYC.