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 Lee
4.89 out of 5 average rating, 236 reviewsCozy Berkshires Cottage
Oct 10 – 17
Home in Chester
4.96 out of 5 average rating, 312 reviewsRiverfront Getaway
Dec 8 – 15
Home in Pittsfield
4.98 out of 5 average rating, 102 reviewsHidden Oasis in the Mountains by Evergreen Home
Jan 9 – 16
Home in Lee
5.0 out of 5 average rating, 234 reviewsBerkshire Mountain retreat with Urban eco-luxuries
Apr 24 – May 1
Home in Dalton
4.99 out of 5 average rating, 121 reviewsCleveland House - renovated Berkshires' gem.
Feb 2 – 9
Home in Monterey
4.93 out of 5 average rating, 116 reviewsPerfect Berkshire getaway.Cozy cottage.Great wifi.
Sep 5 – 12
Home in Dalton
4.92 out of 5 average rating, 171 reviewsBrooksong, the perfect Berkshires getaway
Jan 6 – 13
Home in Chatham
4.9 out of 5 average rating, 145 reviews2BR Chatham Vlg Home Wi-fi Park@Door Keyless 55"TV
Aug 16 – 23
Kid-friendly apartment rentals
Apartment in Lee
4.79 out of 5 average rating, 107 reviewsCozy Berkshire Cottage Style Apartment
Apr 23 – 30
Apartment in Great Barrington
4.95 out of 5 average rating, 318 reviewsPrivate En Suite in Beautiful Victorian
Oct 21 – 28
Apartment in North Adams
4.96 out of 5 average rating, 425 reviewsSteps to MoCA, 2bd + SAUNA!
Apr 12 – 19
Apartment in Copake Falls
4.93 out of 5 average rating, 261 reviewsModern Copake Falls Getaway - 8 Mins to Catamount
Oct 26 – Nov 2
Apartment in Northampton
4.95 out of 5 average rating, 281 reviewsBike Path Hideaway Near Smith, Cooley, Northampton
Oct 15 – 22
Apartment in Bennington
4.93 out of 5 average rating, 529 reviewsThe Octopus's Garden
Jul 29 – Aug 5
Apartment in Shelburne Falls
4.98 out of 5 average rating, 489 reviewsIn town, newly renovated studio with private deck
Mar 31 – Apr 7
Apartment in Adams
4.85 out of 5 average rating, 123 reviewsfull apartment in adams and self check in
Jul 21 – 28
Kid-friendly condo rentals
Condo in North Adams
4.91 out of 5 average rating, 210 reviewsDowntown Flat Iron Condo - walk to MoCA #12
Jun 5 – 12
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
Jun 8 – 15
Condo in Hudson
4.94 out of 5 average rating, 143 reviewsHarmony Valley Home, bright & inviting 2-BR escape
Jan 14 – 21
Condo in West Dover
4.94 out of 5 average rating, 181 reviewsComfy Condo - 2 Min Walk to Carinthia Grommet Lift
Sep 21 – 28
Condo in Albany
4.89 out of 5 average rating, 163 reviewsElegant, spacious studio apt in historic mansion
Jan 5 – 12
Condo in Brattleboro
4.92 out of 5 average rating, 286 reviewsPrivate & Quiet Studio Apt. in Vermont
Oct 26 – Nov 2
Condo in Stratton
4.96 out of 5 average rating, 118 reviewsCozy condo within walking distance to the slopes.
Jun 28 – Jul 5
Condo in Saratoga Springs
4.98 out of 5 average rating, 135 reviewsOwl's Nest - Unique Condo in Vintage Location
Nov 6 – 13
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
ﺩ.ﺇ184 before taxes and fees
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