Kid-friendly holiday 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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Western Massachusetts kid-friendly rentals
Child-friendly house rentals
Home in Dalton
4.88 out of 5 average rating, 114 reviewsThe Yellow House
Home in Southwick
4.99 out of 5 average rating, 182 reviewsLinny's Lakeview Cottage
Home in Chester
4.96 out of 5 average rating, 312 reviewsRiverfront Getaway
Home in Williamsburg
4.99 out of 5 average rating, 159 reviewsHilltown Studio
Home in North Adams
4.99 out of 5 average rating, 272 reviewsSteps to MoCA private house + SAUNA!
Home in Feeding Hills
4.89 out of 5 average rating, 887 reviewsFarm Fresh Feeding Hills
Home in New Lebanon
4.99 out of 5 average rating, 348 reviewsThe old sawmill from 1771
Home in Monterey
4.93 out of 5 average rating, 308 reviewsCharming cottage w/ gorgeous views.
Kid-Friendly apartment rentals
Apartment in Northampton
4.92 out of 5 average rating, 543 reviewsSunny Peaceful Home
Apartment in Shelburne Falls
4.98 out of 5 average rating, 489 reviewsIn town, newly renovated studio with private deck
Apartment in Shelburne Falls
4.95 out of 5 average rating, 147 reviewsSoaring 2-level loft w/ views in heart of downtown
Apartment in Northampton
4.98 out of 5 average rating, 650 reviewsTree Top Suite, cozy downtown apartment
Apartment in Shelburne Falls
4.96 out of 5 average rating, 292 reviewsAnnies’ Place by The Bridge of Flowers ~
Apartment in Hadley
4.97 out of 5 average rating, 215 reviewsSweet Retreat minutes from Northampton & Amherst
Apartment in Greenfield
4.98 out of 5 average rating, 154 reviewsHistoric Greenfield Home: Cozy Private Guest Suite
Apartment in Copake Falls
4.93 out of 5 average rating, 262 reviewsModern Copake Falls Getaway - 8 Mins to Catamount
Child-Friendly Holiday Condos
Condo in Windham
4.89 out of 5 average rating, 134 reviewsCozy Mountain hideaway Windham, Hunter
Condo in Middletown
4.97 out of 5 average rating, 105 reviewsEntire place to yourself Cromwell/Middletown Line
Condo in Brattleboro
4.92 out of 5 average rating, 286 reviewsPrivate & Quiet Studio Apt. in Vermont
Condo in West Dover
4.94 out of 5 average rating, 181 reviewsComfy Condo - 2 Min Walk to Carinthia Grommet Lift
Condo in Lanesville
4.97 out of 5 average rating, 550 reviewsStylish Condo Ski on/ Ski off Hunter Mountain
Condo in Hudson
4.94 out of 5 average rating, 143 reviewsHarmony Valley Home, bright & inviting 2-BR escape
Condo in Hunter
4.97 out of 5 average rating, 428 reviews*Great Reviews* Hunter Mtn. Cozy/Clean/Close Condo
Condo in Hunter
4.98 out of 5 average rating, 538 reviewsHunter Mtn Liftside Ski In/Out, Slopeside!
Destinations to explore
- Cambridge Accommodation & holiday rentals
- New Haven Holiday rentals
- Lake George Accommodation & holiday rentals
- Providence Holiday rentals
- Catskill Holiday rentals
- Albany Holiday rentals
- Philadelphia Accommodation & holiday rentals
- New York Accommodation & holiday rentals
- Jersey City Holiday rentals
- The Hamptons Holiday rentals
- Boston Accommodation & holiday rentals
- Montreal Accommodation & holiday rentals
- Kid-friendly rentals United States
- Kid-friendly rentals Boston
- Kid-friendly rentals New York
- Kid-friendly rentals New Hampshire
- Kid-friendly rentals Massachusetts
- Cabin rentals Western Massachusetts
- Wheelchair accessible rentals Western Massachusetts
- House rentals Western Massachusetts
- Rentals with beach access Western Massachusetts
- Rentals with a hot tub Western Massachusetts
- Rentals with a sauna Western Massachusetts
- Condo rentals Western Massachusetts
- Lakehouse rentals Western Massachusetts
- Pet-friendly rentals Western Massachusetts
- Rentals with breakfast Western Massachusetts
- Ski-in/ski-out rentals Western Massachusetts
- Rentals with pools Western Massachusetts
- Monthly Rentals Western Massachusetts
- Rentals with a washing machine and dryer Western Massachusetts
- Rentals with outdoor seating Western Massachusetts
- Cottage rentals Western Massachusetts
- Family-friendly rentals Western Massachusetts
- Guesthouse rentals Western Massachusetts
- Chalet rentals Western Massachusetts
- Rentals with an EV charger Western Massachusetts
- Rentals with lake access Western Massachusetts
- Bed and breakfasts Western Massachusetts
- Holiday home rentals Western Massachusetts
- Rentals with a patio Western Massachusetts
- Hotel rentals Western Massachusetts
- Rentals with a fireplace Western Massachusetts
- Rentals with a home theatre Western Massachusetts
- Fitness-friendly rentals Western Massachusetts
- Farmstay rentals Western Massachusetts
- Rentals with a kayak Western Massachusetts
- Private suite rentals Western Massachusetts
- Boutique hotel rentals Western Massachusetts
- Townhouse rentals Western Massachusetts
- Beachfront rentals Western Massachusetts
- Smoking-friendly rentals Western Massachusetts
- Apartment rentals Western Massachusetts
- Rentals with a fire pit Western Massachusetts
- Waterfront rentals Western Massachusetts
- Rentals with an accessible height toilet Western Massachusetts
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
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- Holiday Apartments Australia
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- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
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- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
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- Beach Houses United Kingdom
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- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
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- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom