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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Western Massachusetts family-friendly rentals
Kid-friendly house rentals
Home in Dalton
4.88 out of 5 average rating, 114 reviewsThe Yellow House
Home in Chester
4.96 out of 5 average rating, 312 reviewsRiverfront Getaway
Home in Southwick
4.99 out of 5 average rating, 182 reviewsLinny's Lakeview Cottage
Home in Williamsburg
4.99 out of 5 average rating, 159 reviewsHilltown Studio
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 North Adams
4.99 out of 5 average rating, 271 reviewsSteps to MoCA private house + SAUNA!
Home in Monterey
4.93 out of 5 average rating, 308 reviewsCharming cottage w/ gorgeous views.
Family-friendly apartment rentals
Flat in Shelburne Falls
4.98 out of 5 average rating, 489 reviewsIn town, newly renovated studio with private deck
Flat in Petersburg
4.85 out of 5 average rating, 150 reviewsThe Beer Diviner Brewery Apartment
Flat in Shelburne Falls
4.96 out of 5 average rating, 292 reviewsAnnies’ Place by The Bridge of Flowers ~
Flat in Northampton
4.98 out of 5 average rating, 650 reviewsTree Top Suite, cozy downtown apartment
Flat in Copake Falls
4.93 out of 5 average rating, 262 reviewsModern Copake Falls Getaway - 8 Mins to Catamount
Flat in Hadley
4.97 out of 5 average rating, 215 reviewsSweet Retreat minutes from Northampton & Amherst
Flat in Greenfield
4.98 out of 5 average rating, 154 reviewsHistoric Greenfield Home: Cozy Private Guest Suite
Flat in Brimfield
4.98 out of 5 average rating, 142 reviewsQuiet & Cozy Main Street Retreat
Family-friendly apartment rentals
Apartment in Brattleboro
4.92 out of 5 average rating, 286 reviewsPrivate & Quiet Studio Apt. in Vermont
Apartment in West Dover
4.94 out of 5 average rating, 181 reviewsComfy Condo - 2 Min Walk to Carinthia Grommet Lift
Apartment in Middletown
4.97 out of 5 average rating, 105 reviewsEntire place to yourself Cromwell/Middletown Line
Apartment in Hudson
4.94 out of 5 average rating, 143 reviewsHarmony Valley Home, bright & inviting 2-BR escape
Apartment in Poughkeepsie
4.97 out of 5 average rating, 224 reviewsSpacious and stylish entire one bedroom apartment.
Apartment in Saratoga Springs
4.98 out of 5 average rating, 136 reviewsOwl's Nest - Unique Condo in Vintage Location
Apartment in Stratton
4.94 out of 5 average rating, 138 reviewsUpdated Ski in/Ski out Stratton Condo!
Apartment in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
Destinations to explore
- Cambridge Holiday rentals
- New Haven Holiday rentals
- Lake George Holiday rentals
- Providence Holiday rentals
- Catskill Holiday rentals
- Albany Holiday rentals
- Philadelphia Holiday rentals
- New York Holiday rentals
- Jersey City Holiday rentals
- The Hamptons Holiday rentals
- Boston Holiday rentals
- Montreal Holiday rentals
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