Kid-friendly holiday rentals in Western Massachusetts

Find and book unique family-friendly rentals on Airbnb

Top-rated family-friendly rentals in Western Massachusetts

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

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Guest favourite

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 favourite

Home in Lake Katrine

4.95 out of 5 average rating, 111 reviews

Waterfront 3BR Home in Hudson Valley, Catskills

Key Residence Features at a glance; Waterfront on the Esopus Creek, Seasonal Kayaks, Rowboat, Dock (approx. Memorial Day weekend-mid October) large yard. Fully equipped kitchen, cable, wireless internet, washer and dryer. Enclosed porch, deck and patio with propane grill and patio furniture. Paved flat driveway, ramp allowing access to first floor, oversize door to first floor bathroom. Three spacious bedrooms with air conditioners. Convenient location close to thruway exits. No boat launch.

Superhost

Home in Windham

4.87 out of 5 average rating, 113 reviews

Magic Creek

Come enjoy our brand new hot tub! Magic Creek is quintessential Vermont- an antique made modern. The cozy living room with fireplace is an ideal spot to gather at the end of your day. The house has 3 bedrooms and a play room that doubles as a guest room. The house is bordered by a creek with peaceful water falls. Centrally located in the heart of ski country, minutes to Magic Mountain, 20 minutes to Bromley, and 30 to Stratton or Mt Snow, and 40 minutes to Okemo. Come and enjoy it all.

Superhost

Home in Antrim

4.81 out of 5 average rating, 125 reviews

Quiet House in the Woods

Relax with the whole family at this peaceful place to stay. - Gregg Lake 5 mins away (Swim, Volleyball, Swings, Boat Docks) - Great hiking trails (Monadnock & Miller State Park) - Ski in the winter (Crotched Mountain 20 mins away, Pats Peak 30 mins away) - Small town: Mom & Pop shops/restaurants, Antique stores - 2 Decks: Out door dining & sitting areas This is not an investment property, this is my home. Please be respectful of the property. Thank you! Hope you enjoy your stay!

Superhost

Flat in Beacon

4.85 out of 5 average rating, 104 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 favourite

Home in Kerhonkson

4.95 out of 5 average rating, 354 reviews

Beautiful Salt Water Pool & Fully Fenced 10 Acres

Look from the luxurious spa tub at the countryside oasis atop a rolling knoll on the edge of fir-scented forest land. Come home from a hike, farm, or award winning restaurant, & snuggle up by the fire under grand cathedral ceilings. In summer, swim in the salt water pool & enjoy the fire pit surrounded by lush landscaping & quiet. Stunning views as the seasons change, the windows showcasing rolling snowy hills or the vibrant colors of autumn leaves climbing the mountains.

Guest favourite

Home in Bristol

4.92 out of 5 average rating, 171 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.

Guest favourite

Cabin in Accord

4.94 out of 5 average rating, 112 reviews

Peaceful Cabins by the river, excellent wifi!

Just figured out availability for our cabins this summer! The Big Cabin, located 15 feet from the water’s edge, will easily sleep six. The Little Cabin, 30 yards from the House with a water view and plenty of privacy, is perfect for a couple. Located on a secluded, non-thoroughfare road, it includes access to a private swimming hole and waterfall. Near the Shawangunk climbing mountain and hiking/cycling trails, Accord “downtown” and super chic Inness.

Guest favourite

Home in Palenville

4.96 out of 5 average rating, 162 reviews

Serenity Retreat: Mountains, Waterfalls, Comfort

Enjoy a tranquil retreat overlooking a peaceful creek, set against gorgeous mountain views and nearby spectacular waterfalls. Just a short drive from Woodstock and Saugerties, NY this home on a serene country lane is a gateway to nature's beauty. With close proximity to local attractions, a lush garden, stunning mountain vistas, and a family-and-pet-friendly yard featuring a fire pit and bad mitten, it's the perfect blend of comfort and adventure.

Guest favourite

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.

Superhost

Flat in Gansevoort

4.78 out of 5 average rating, 120 reviews

Cozy, Pets, Coffee, B-Ball, Fire Pit, BBQ

⭐"Cozy, clean and affordable! Highly recommend." -Alison 🏡 Family Style Apartment 🛏️ Sleeps 3 🏀 Basketball Court 🔥 Fire Pit 💻High speed internet 🚽 Heated Bidet 🐶 Pets 🌲 Front yard 🔥 BBQ 🏠Patio with Sun Loungers 🚗 Convenient Parking 📍 15 min to Saratoga Springs, 20 min to Lake George 🍽️ Fully Equipped Kitchen ☕Coffee, Tea & Decaf Note: Potential for noise from upstairs guests

Guest favourite

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!