Kid-friendly vacation rentals in Pittsfield

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Pittsfield

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

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Guest favorite

Cottage in Valatie

4.99 out of 5 average rating, 141 reviews

Kinderhook Lake Retreat-kayaks/SUP/central air

Welcome to our paradise-where time slows down and memories are made. It's the perfect retreat for relaxing, kayaking, swimming, hiking, biking, and so much more. -Sip your coffee on the decks while enjoying lake wildlife -Grab a kayak or paddleboard and explore the bays, coves and creeks -Catch the sunset, then end the day sharing stories around the starlit firepit An ideal base for exploring restaurants, breweries, wineries, galleries, historical sites, trails, farm stores, and orchards.

Guest favorite

Home in Pittsfield

4.97 out of 5 average rating, 106 reviews

Berkshire Pontoosuc Lake- Modern and Updated

Lakefront Home for Rent. This home has been 100% remodelled! With a beautiful spot directly on Pontoosuc, the new kitchen, bathrooms, fireplace, and glass enclosed family room all benefit from the idyllic scenery. The home has 5 bedrooms and a convertible playroom with a futon for even more space. 2 bedrooms have bunk beds plus a full size bed in them. 2 bedrooms have king size beds and 1 has a queen. The master suite has an en-suite bathroom and a balcony overlooking the lake. Many upgrades!

Guest favorite

Cottage in Ancram

4.99 out of 5 average rating, 173 reviews

Lake View & Pet Friendly Wood Burning Fireplace

All size Dogs & Cats Welcome *Outside backyard is large and surrounded by trees with Firepit, Hammock & Volleyball Net +Watercraft available - Kayaks/Rowboat Swim Platform Indoor Wood Burning Fireplace Fully stocked kitchen and toiletries 10-15 minutes to Bash Bish Falls/Catamount Aerial Park/Ski/Snowboard/Tubing 25-30 minutes to Berkshires Shoe shoeing +November-April: watercraft not available, also weather dependent *Only one neighbor, is to the left, separated by trees and bushes

Superhost

Cottage in Hudson

4.84 out of 5 average rating, 128 reviews

Peaceful waterfront getaway near Hudson, NY

Love nature? Enjoy your own entire home on the Stockport Creek with private kayak/boat launch to the Hudson River. Hiking and bike trails nearby. You are immersed in Columbia County’s rural beauty between the Berkshires and the Catskills with Hudson’s hopping food and art scene minutes away. OMI sculpture park, Olana, Chatham, farm markets, and Warren Street are a short drive. Ski Hunter or Catamount inside an hour. Cozy wood burning stove as well as outdoor fire pit. Minimum 3 day stay.

Guest favorite

Home in Wilmington

4.96 out of 5 average rating, 106 reviews

Family SKI Retreat inWilmington-Walk 2Town-Hot Tub

Welcome to our family-friendly home in Wilmington, Vermont! Perfect for group getaways. Our home offers a blend of comfort and convenience. Just a short walk from Wilmington's charming downtown, with easy access to restaurants, shops, and groceries. Mount Snow is only a 12-minutes away, making this an ideal base for both winter skiing adventures and summer hikes. Whether you're here for outdoor fun or cozy nights by the fire pit, our home is ready to make your Vermont getaway unforgettable!

Guest favorite

Home in Athens

4.93 out of 5 average rating, 114 reviews

Lake house, 700 ft waterfront - from every room

Panoramic views from the wrap-around deck offers privacy and 700 feet of lake frontage from this comfortable home. Enjoy the sunrise and sunsets views of the lake from EVERY room. Two kayaks, canoe, paddle board to be enjoyed from its private beach. The great room has full lake view, heated floors and two large decks. This home offers 4 bedrooms, 2 and 1/2 baths, a finished lower level that features game room with private deck, ping pong table, giant Jenga, home gym, and large 55in TV.

Guest favorite

Home in North Adams

5 out of 5 average rating, 103 reviews

Berkshires Retreat! in the woods, yet in town!

We are happy to share our piece of heaven in the Berkshires! Newly renovated 4-bedroom 2-1/2-bathroom vacation rental nested in 2.7 acres of woods, yet conveniently located in the city of North Adams. A 5 minute walk from Windsor Lake, a 15 minute walk to MASS MoCA, and a close drive to many restaurants. The house is kid friendly, basketball hoop, soccer goal, and games. We are close to ski resorts, as well hiking and biking trails, including Mount Greylock. PET FEE. PERMISSION NEEDED.

Guest favorite

Home in Athens

4.83 out of 5 average rating, 169 reviews

A Victorian "Lady"

Enjoy an old-fashioned vacation right across the street from the Hudson river. Watch the tides, boats, and barges pass by. Dining, kayaking within walking. Historic Hudson, Olana just 10 min. drive. This is a house to relax, use as a base for other activities. It is not intended as a place to party.. It is a quiet neighborhood. I expect my guests to respect that. There is a weekend special. If you book friday/saturday or saturday/sunday the price is $350.00 for the 2 nights. Thanks

Guest favorite

Bungalow in Great Barrington

4.91 out of 5 average rating, 116 reviews

Idyllic Berkshires Getaway

Secluded large ranch in the country on 8 acres with pastoral scenic views, only 7 minutes drive from the center of Great Barrington and Lake Mansfield Beach, 10 minutes to Ski Butternut, 12 minutes to Stockbridge, 20 minutes to Lenox and Tanglewood . Kids playroom and a spectacular jungle gym, perfect for entertaining inside by the fire or outside on the patio with the bbq with beautiful views surrounded by pine trees. Perfect for fall foliage, skiing, spring and summer!

Guest favorite

Home in Hillsdale

4.91 out of 5 average rating, 114 reviews

Fenced yard, playroom & the Berkshires - $0 fees

Enjoy our 8.5 acre, private home. It's a great place to either relax, or enjoy nature whether it's skiing, hiking, kayaking, or biking. Ample space for numerous groups, including an enclosed backyard with grill and fire pit. 4 bedrooms and 3 baths For hikers, Taconic State Park :06 For bikers, Harlem Vally Rail Trail :08 For skiers, Catamount :05 ~2.5 hours from NYC and Boston ~ 15 min to Great Barrington, MA ~25 min to Hudson, NY ~20 min to Millerton, NY

Superhost

Tiny home in Nassau

4.94 out of 5 average rating, 141 reviews

Tiny Home 2 hrs NYC and BOS Lakefront WIFI

Extended stays are welcome! *** IMPORTANT *** Our photos previously showed screens enclosing the porch, but we have removed them due to wear from pets. Maintaining a pet-friendly environment is important to us, so the screens are no longer part of the tiny house. Enjoy a stay in our clean, charming, unique tiny home. This waterfront property features a private peninsula with a sandy entrance to the water.

Guest favorite

Home in Copake

4.96 out of 5 average rating, 191 reviews

Lakefront +views +skiing +bbq +firepit +games

With all of the craziness in life, this is the place you go to wake up in the morning to sip your coffee and do everything or nothing. This is the best location on Robinson Pond with beautiful views and access to the private beach and deepest part of the lake. Clear your headspace and enjoy this year-round escape with four seasons of activities and a cozy home to remind you of the greater things in life.