
Family-friendly vacation rentals in Massachusetts
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Massachusetts
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Cider House Cottage
Antique guest cottage on a becountry 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

Annisquam Village Bunny Cottage
This beautiful Annisquam Village cottage was renovated to the highest level of quality by two artist's. Located just 5 minutes from Lighthouse Beach, Cambridge Beach and Talise Restaurant. Bunny Cottage has beautiful gardens, is surrounded by water on 3 sides, and has peek-a-boo views of Wingaersheek Beach from the bedroom window. The house is charming, with top notch amenities, like, heated floors, air conditioning (indoor/outdoor living). Mass Dept. of Revenue Certificate Number: #C0022781070

Seaside Cottage
Here you are down the street from some of Marblehead's hidden gems such as Redds Pond, Browns Island & Old Burial Hill Cemetery. One car parking. 5 minute walk to the beach, shops & restaurants. Fully fenced in yard with turf grass. One bedroom with a low profile queen sized bed. In unit washer/dryer. Full bath with tub. Newly renovated kitchen with major appliances: stove, oven, dishwasher, fridge, Nespresso maker & microwave. Sheets & bath linens provided. Minisplit A/C. Home is all one level.

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

Lakefront, view of ski mtn, fireplace, sauna
Direct lakefront with panoramic views of Wachusett Mountain (#1 skiing in MA). In the summer, enjoy the kayaks, canoe, paddle-boards, motor boat. In the winter, cozy up next to the fireplace and enjoy a complimentary bottle of wine. In the fall, gaze upon the breathtaking foliage from the sunroom. Outdoor shower, dock, firepit, hammock, bike, washer/dryer, desk, sauna, dishwasher, linens, kitchen amenities. Our other lakefront house is down the road: www.airbnb.com/h/lakefrontmountainview

Enchanted Tiny Tower nestled in the Berkshires
Whimsical and romantic tower on the Santarella Estate in Tyringham, MA in the heart of the Berkshires. Live out your fairytale in this two-story unique, tiny home. First floor offers 3 rooms in one with kitchenette, sitting area, and dining room looking out on to the babbling brook. Upper bedchamber with canopied bed provides amazing views of sky and trees through massive, mill windows. Perfect destination for a relaxing getaway or special stay while exploring all the Berkshires has to offer.

Little Boho Retreat by the Beach
Kick back and relax in the most calming, low charm country, coastal cottage the town of Marion has to offer. You’ll experience spectacular view of the beach right from the deck to watching the boats from the harbor. Don’t just limit yourself to life at the beach in just the summer months, come and make memories in this beautiful year-round cozy cottage. It's a perfect retreat to go swimming, kayaking, fishing, bird/seal/crabs watching and more right here in a private community on Dexter Beach.

Serene 1-br suite on 75 acre horse property
Find your peaceful retreat in our 1-bedroom suite, situated on a serene 75-acre horse property with scenic nature trails. Enjoy a private entrance, dedicated workspace, and complimentary high-speed WiFi, making it an ideal haven for remote workers. Take in the picturesque views of our horse pastures, with up to 20 horses, right from your windows. Our property is nestled in the woods, about 1/3 mile from the main road. Located near Amherst, Hampshire, UMass, Smith, and Mt. Holyoke colleges.

The little house on Mirror Pond
Escape to our fully renovated tiny pond house on the serene Mirror Pond. Perfect for up to 4 guests, enjoy swimming, kayaking, or floating on tubes. Unwind by the fire pit, barbecue on the deck, or cozy up by the fireplace (our apologize but it is currently not working) with board games on cooler days. With great WiFi, it’s also ideal for a peaceful work retreat. Whether you're here to relax, or get some work done, this tranquil hideaway offers the perfect blend of adventure and relaxation.

Winery Studio w/ Private Hot Tub & Wine Tasting
Private Hot Tub, Vineyard Guesthouse at Winery. This former art studio is a true getaway to relax & feel at peace. Filled with natural light, it sits beside one of our historic 1800s barns on the winery property with vineyard views. Perfect for a romantic retreat or the traveling professional seeking a peaceful home away from home. Located in an affluent neighborhood minutes from shopping & restaurants. Your stay includes a complimentary wine tasting and 10% off all wine bottle purchases

Bedroom Forest View I Sauna I Fire-pit I Trails
Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

Mink Cove Treehouse
A unique adult adventure awaits in this cozy hand crafted tree house! Nestled 12 feet off the ground amongst the chirping birds, red oaks & breathtaking views of Mink Cove in Buzzards Bay. The tree house is accessible by a suspension bridge that leads you to a partially covered porch where you can enjoy a cup of coffee or sit back & take in the sunset with a glass of wine. Step inside to the living space & snuggle up on the couch for an intimate evening.
Popular amenities for Massachusetts family-friendly rentals
Family-friendly home rentals with a hot tub

Violet’s Place- king bed- pet friendly- hot tub!

The Creation Station

Local Beach+ Fireplace + Hot Tub Under the *Stars*

Historic 1 Bed/In Town/Best Location/Hot tub/deck

Jaw dropping mountain & lake views

Peaceful Lake Views from Private Hot Tub & Kayaks

Cozy Lake Cottage: Hot Tub, Gym & Waterfront Views

John Alden Condo
Family- and pet-friendly home rentals

Beach Cottage, without going over bridges to Cape!

Trainmaster's Inn - Caboose

Tiny farm house on horse farm

#7 Spacious Modern Home Near Boston w/ Parking

Harbor View Suite

Pirates Hideaway - Sanctuary on the Marsh

Upper Cape Cozy Cottage

Lovely Lakeside Cottage
Family-friendly home rentals with a pool

Nana-tucket Inn

Hopkinton Mass 3+ Bedrooms - Great location!

Courtyard Garden | Pool | BBQ+Fire Tbl | Fireplace

Spacious vacation unit in premium suburban town

Country Cottage in the City

Seaview Summit | Ocean Views, Indoor Pool, Beach

In-law Apartment, Full Kitchen, Near Mt Wachusetts

Steps from Harbor, Pool, Backyard Garden, Parking
Destinations to explore
- Guesthouse rentals Massachusetts
- Ski-in/ski-out rentals Massachusetts
- Rentals with pools Massachusetts
- Rentals with a washer and dryer Massachusetts
- Beach house rentals Massachusetts
- Rentals with a kayak Massachusetts
- Smoking-friendly rentals Massachusetts
- Vacation home rentals Massachusetts
- Pet-friendly rentals Massachusetts
- Cottage rentals Massachusetts
- Rentals with a home theater Massachusetts
- Rentals with an accessible height toilet Massachusetts
- RV rentals Massachusetts
- Rentals with breakfast Massachusetts
- Townhouse rentals Massachusetts
- Barn rentals Massachusetts
- Rentals with a sauna Massachusetts
- Rentals with a hot tub Massachusetts
- Beachfront rentals Massachusetts
- House rentals Massachusetts
- Villa rentals Massachusetts
- Farmstay rentals Massachusetts
- Fitness-friendly rentals Massachusetts
- Rentals with a fire pit Massachusetts
- Waterfront rentals Massachusetts
- Luxury rentals Massachusetts
- Chalet rentals Massachusetts
- Lakehouse rentals Massachusetts
- Rentals with a fireplace Massachusetts
- Mansion rentals Massachusetts
- Cabin rentals Massachusetts
- Condo rentals Massachusetts
- Bungalow rentals Massachusetts
- Campsite rentals Massachusetts
- Rentals with a patio Massachusetts
- Apartment rentals Massachusetts
- Hotel rooms Massachusetts
- Tiny house rentals Massachusetts
- Rentals with outdoor seating Massachusetts
- Serviced apartment rentals Massachusetts
- Rentals with an EV charger Massachusetts
- Rentals with beach access Massachusetts
- Boutique hotels Massachusetts
- Boat rentals Massachusetts
- Resort rentals Massachusetts
- Aparthotel rentals Massachusetts
- Private suite rentals Massachusetts
- Nature eco lodge rentals Massachusetts
- Bed and breakfasts Massachusetts
- Rentals with an accessible height bed Massachusetts
- Loft rentals Massachusetts
- Rentals with lake access Massachusetts
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