Kid-friendly vacation rentals in Pittsfield
Find and book unique kid-friendly rentals on Airbnb
Top-rated kid-friendly rentals in Pittsfield
Guests agree: these kid-friendly rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Pittsfield kid-friendly rentals
Kid-friendly house rentals
Home in Chester
4.96 out of 5 average rating, 311 reviewsRiverfront Getaway
Dec 7 – 14
Home in Lee
5.0 out of 5 average rating, 230 reviewsBerkshire Mountain retreat with Urban eco-luxuries
Apr 22 – 29
Home in North Adams
4.99 out of 5 average rating, 266 reviewsSteps to MoCA private house + SAUNA!
Jan 15 – 22
Home in Lee
4.89 out of 5 average rating, 236 reviewsCozy Berkshires Cottage
Oct 19 – 26
Home in Dalton
4.92 out of 5 average rating, 171 reviewsBrooksong, the perfect Berkshires getaway
Oct 24 – 31
Home in Chatham
4.9 out of 5 average rating, 145 reviews2BR Chatham Vlg Home Wi-fi Park@Door Keyless 55"TV
Dec 3 – 10
Home in Dalton
4.99 out of 5 average rating, 120 reviewsCleveland House - renovated Berkshires' gem.
Nov 5 – 12
Home in Canaan
4.95 out of 5 average rating, 202 reviewsHudson River Valley/Berkshires
Dec 9 – 16
Kid-friendly apartment rentals
Apartment in Petersburg
4.85 out of 5 average rating, 149 reviewsThe Beer Diviner Brewery Apartment
Jan 16 – 23
Apartment in Great Barrington
4.95 out of 5 average rating, 318 reviewsPrivate En Suite in Beautiful Victorian
Dec 11 – 18
Apartment in Bennington
4.93 out of 5 average rating, 527 reviewsThe Octopus's Garden
Oct 16 – 23
Apartment in Copake Falls
4.93 out of 5 average rating, 258 reviewsModern Copake Falls Getaway - 8 Mins to Catamount
Oct 14 – 21
Apartment in Shelburne Falls
4.95 out of 5 average rating, 146 reviewsSoaring 2-level loft w/ views in heart of downtown
Jul 6 – 13
Apartment in Shelburne Falls
4.98 out of 5 average rating, 488 reviewsIn town, newly renovated studio with private deck
Apr 25 – May 2
Apartment in Adams
4.85 out of 5 average rating, 123 reviewsfull apartment in adams and self check in
Jun 30 – Jul 7
Apartment in Williamstown
4.93 out of 5 average rating, 236 reviewsCOLD SPRING
Jul 19 – 26
Kid-friendly condo rentals
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
May 30 – Jun 6
Condo in North Adams
4.91 out of 5 average rating, 209 reviewsDowntown Flat Iron Condo - walk to MoCA #12
Jun 16 – 23
Condo in Hudson
4.94 out of 5 average rating, 142 reviewsHarmony Valley Home, bright & inviting 2-BR escape
Jun 9 – 16
Condo in Albany
4.89 out of 5 average rating, 162 reviewsElegant, spacious studio apt in historic mansion
Oct 18 – 25
Condo in Brattleboro
4.92 out of 5 average rating, 286 reviewsPrivate & Quiet Studio Apt. in Vermont
Aug 24 – 31
Condo in West Dover
4.94 out of 5 average rating, 181 reviewsComfy Condo - 2 Min Walk to Carinthia Grommet Lift
Sep 6 – 13
Condo in Stratton
4.96 out of 5 average rating, 118 reviewsCozy condo within walking distance to the slopes.
Jun 12 – 19
Condo in Saratoga Springs
4.98 out of 5 average rating, 135 reviewsOwl's Nest - Unique Condo in Vintage Location
Nov 23 – 30
Quick stats about vacation rentals that are kid-friendly in Pittsfield
Total rentals
40 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
1.8K reviews
Nightly prices starting at
$50 before taxes and fees
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