Kid-friendly vacation rentals in Western Massachusetts

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Western Massachusetts

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

0 of 0 items showing

1 of 3 pages

Guest favorite

A wooden deck is shown featuring a large umbrella providing shade over a seating area. A patterned rug lies on the floor, accompanied by a potted plant. Two lounge chairs and a small table create a comfortable outdoor space, surrounded by lush greenery.

Cabin in Saugerties

4.87 out of 5 average rating, 183 reviews

Private Woodstock Getaway w Hot Tub

Relax in this cozy retreat on a private road. Snuggle up by the fire, play some records, relax on the sunny deck, or jump in the hot tub. Cook dinner in the fully stocked kitchen or grill on the deck and enjoy your meal in the screened in porch. The master bedroom has a king-size bed and quality linens, as do the other two bedrooms, one with a queen and one with 2 twins beds. Relax downstairs in the family room, watch a movie, or cozy up by the wood burning stove. Short drive to the town of Woodstock ! Close to skiing, hiking & swim holes! $50 extra for dogs. No cats. Use hot tub at your own risk. The whole home is yours except the garage remains closed. Always available if any issues arise, but not on the property. The house is set back on a private road. It's a genuine retreat, but still only a short drive from the shops and restaurants of Woodstock and Saugerties. Local hikes abound, and venture a little further to find swimming holes and skiing. If you have a small child, I suggest bringing a gate as there are stairs to the basement.

Top guest favorite

A wooden playground structure is equipped with a blue slide, climbing wall, and two swings. The setting features a grassy area surrounded by trees with autumn leaves, providing a serene outdoor space for children to play.

Home in Saugerties

4.98 out of 5 average rating, 50 reviews

A Perfect Upstate Family Getaway with a Pool

This large family friendly house is the perfect place to relax and unwind with your loved ones. With 5 bedrooms, a spacious backyard, and a swimming pool, there's something for everyone to enjoy. The house is located in a quiet neighborhood, just a short drive from downtown Saugerties, Woodstock and Kingston. The backyard is the perfect place to relax and entertain. There's a large patio with plenty of seating, a swimming pool, and a playground. There is Central air and a grill is available.

Superhost

A spacious living area features a large, soft sofa with decorative pillows, facing a rustic coffee table. Natural light fills the room through multiple windows, with a dining table set for six in the background. Soft, neutral tones create a serene atmosphere.

Home in Cornwall

4.82 out of 5 average rating, 96 reviews

State Forest Getaway

Enjoy our Mountain getaway for year round fun! There are lots of activities close by-Mohawk Ski Mountain, Indian Lake and historic Covered Bridges! Hike in the backyard, cool off in the creek or relax in front of the Wood-burning fireplace or get the whole family together for a fun BBQ on the outdoor deck. We have 4 comfortable bedrooms plus daybed room and 3 bathrooms and a fully equipped Chefs Kitchen. The living room is great for lounging and perfect a movie night watched on the projector

Top guest favorite

An outdoor deck is presented with a large umbrella providing shade over a dining table set for four. Two stylish chairs complement the table, surrounded by lush greenery, with a glimpse of a small shed in the distance.

Home in Wappingers Falls

4.96 out of 5 average rating, 26 reviews

Caroline House Beacon Getaway

Set just outside Beacon in a beautiful, quiet neighborhood, this is the perfect retreat for family and friends after a fun day at all of the local attractions. Enjoy the large outdoor space with firepit, grill, hammock and deck or any of the close by farms, breweries, downtown Beacon and the many Hudson River adventures. Just 7 minutes from the Beacon MTA train and I84 with all the excitement at your fingertips set in a beautiful neighborhood where you may spot our neighbors horses roaming.

Superhost

A well-equipped kitchen features modern appliances, including a refrigerator and oven, within bright white cabinetry. A wooden dining table with chairs sits in the foreground, while hardwood flooring enhances the spaciousness. Natural light illuminates the room from a nearby window.

Apartment in Beacon

4.85 out of 5 average rating, 105 reviews

Lovely 2 bed, 2 full bath. & private yard getaway

Bring the whole family to this super clean place with lots of room for fun. Private Yard ! kitchen/ dining room, living room, main bedroom w/king size bed & private bathroom, kid’s bedroom w/queen size bed & full bathroom across the room. This beautiful Airbnb has prime location. Across the street you will find the beautiful Madam Brett park w/waterfall and walking trail. Close to main street, train station, MT. Beacon also 8 min drive to Bannerman Castle and Dia Beacon Museum.

Guest favorite

A serene lakeside view captures vibrant fall colors mirrored in calm waters. The shoreline is lined with trees displaying bright reds and oranges against lush green foliage, while a clear sky with soft clouds reflects above, complementing the tranquil atmosphere.

Home in Harrisville

4.9 out of 5 average rating, 10 reviews

Harrisville Lake House - A Tranquil Get-Away

Welcome to Harrisville Lake House, a tranquil lakeside retreat for family and friends on the shore of Harrisville Pond. Our cherished home is perfect for a week-long escape, where nature’s beauty meets the warmth of a family home. Our home is a treasure trove of antique furniture, worldly keepsakes, and artwork. Fall colors in September and early October are breathtaking! From the haunting call of loons to the majestic flight of bald eagles, nature is a daily delight!

Guest favorite

A spacious backyard is presented, featuring a playground set with a slide and a small playhouse. A wooden deck offers seating, while a shaded area is created by a large tree. A red shed is visible in the background, surrounded by well-maintained grass.

Home in Bristol

4.92 out of 5 average rating, 172 reviews

Cozy Family Home - Kid & Pet Friendly

3 bedroom house on a quiet street. 5mins down the road from ESPN and Lake Compounce. Kid friendly. Pet friendly. Workspace available. 1 bedroom w/ king bed. 1 bedroom w/ queen bed. 1 bedroom w/ 2 twin beds. Fully finished basement with 60inch TV, kids toys and fitness equipment/stationary bike. Deck and below deck hang out space. Though we aren’t living here full time, it’s still the place we call home, and we will use it when it’s not booked. Long stays welcome.

Top guest favorite

A cozy living room features two soft sofas, one adorned with decorative pillows, arranged around a wooden coffee table. A patterned area rug lies beneath, adding warmth. Natural light enters through a window, partially covered by light curtains, and a piece of artwork hangs on the wall.

Apartment in Northampton

5 out of 5 average rating, 44 reviews

Downtown 2 BR 1.5 Bath Townhouse Retreat 3 beds

Conveniently located townhouse that is a short walk to restaurants and shops. Easy access to public transportation with a bus stop by the end of the street. Wi-Fi, a full kitchen, living room, 1/2 bath and laundry, on the first floor. The second floor has a shower, bedroom #1 has a queen bed and bedroom #2 has a queen and a twin. A/C units during summer months. Off street parking and self check in. Pack n play and toddler bed available upon request.

Top guest favorite

A bright living area showcases a gray sofa against a backdrop of high wooden ceilings and natural light filtering through large glass doors. A spiral staircase leads to an upper level, complemented by decorative elements such as a wall clock and potted plants.

Home in Canaan

4.96 out of 5 average rating, 51 reviews

Private Retreat: Hot Tub! Movie Room! Pool Table!

SUMMER: Stay includes: Access to Queechy Lake’s private beach. Sprawl out in this charming home that’s both private and close to everything! Discover everything this ALL SEASON Berkshires/Hudson Valley home has to offer. From skiing to Tanglewood, local farms to wineries, you’re close to it all! Relax in the hot tub lakeside while watching the beavers, curl up by the wood-burning stove, or play a game of pool. You’ll never want to leave!

Guest favorite

An air hockey table is presented in a loft area with muted carpet. The table is set against a backdrop of a wooden railing and features framed photographs mounted on the wall, showcasing serene landscapes.

Townhouse in Tannersville

4.94 out of 5 average rating, 155 reviews

Family-friendly 3BR 2BA Hunter Mnt Townhome

Escape the city with this family-friendly 3-bedroom (including loft), 2-bath Catskills vacation rental with scenic views located only 2 hours away from NYC. You’ll be within 1 mile of Tannersville’s Main Street lined with lots of restaurants and antique shops, 4 miles to Hunter Mountain and 13 miles to Windham Mountain as well as other nearby attractions. Perfect for families or small group of friends.

Guest favorite

Home in Narragansett

4.86 out of 5 average rating, 116 reviews

Hot New home beach access, perfect for families!

This home perfect for families and larger groups! Located in Pettaquamscutt Lake Shores neighborhood of Narragansett with access to private narrow river beach. We've created a true home away from home with a family game room, A fully stocked eat in kitchen, and several amenities for families with children including a double stroller, pack n play, baby bath and children's room with toys!

Guest favorite

A well-maintained private yard features lush green grass, a vibrant hammock for relaxation, and a stone path leading through flower beds. A cozy seating area with woven chairs and a decorative rug is positioned near the apartment, surrounded by trees for added privacy.

Apartment in Carmel-by-the-Sea

4.87 out of 5 average rating, 297 reviews

Private space, with yard

A little bit country with a modern twist, the space provides comfortable sleeping for up to five guests with a queen bed, queen sofa, and an extra twin mattress (if requested). Has many kitchen amenities. You will have a private yard (table, chairs, and grill) plus 5 peaceful acres and short hiking trails to explore. Pet friendly for additional fee.