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, 312 reviewsRiverfront Getaway
Oct 14 – 21
Home in Lee
5.0 out of 5 average rating, 231 reviewsBerkshire Mountain retreat with Urban eco-luxuries
Apr 20 – 27
Home in Lee
4.89 out of 5 average rating, 236 reviewsCozy Berkshires Cottage
May 8 – 15
Home in North Adams
4.99 out of 5 average rating, 266 reviewsSteps to MoCA private house + SAUNA!
Jan 27 – Feb 3
Home in Dalton
4.92 out of 5 average rating, 171 reviewsBrooksong, the perfect Berkshires getaway
Sep 29 – Oct 6
Home in Dalton
4.99 out of 5 average rating, 121 reviewsCleveland House - renovated Berkshires' gem.
Mar 16 – 23
Home in Monterey
4.93 out of 5 average rating, 307 reviewsCharming cottage w/ gorgeous views.
Jan 14 – 21
Home in Lenox
4.93 out of 5 average rating, 210 reviewsHeart of Lenox Walk to Town Cozy Cottage!
May 9 – 16
Kid-friendly apartment rentals
Apartment in Petersburg
4.85 out of 5 average rating, 149 reviewsThe Beer Diviner Brewery Apartment
Mar 18 – 25
Apartment in Lee
4.79 out of 5 average rating, 107 reviewsCozy Berkshire Cottage Style Apartment
Apr 17 – 24
Apartment in Great Barrington
4.95 out of 5 average rating, 318 reviewsPrivate En Suite in Beautiful Victorian
Feb 14 – 21
Apartment in Copake Falls
4.93 out of 5 average rating, 260 reviewsModern Copake Falls Getaway - 8 Mins to Catamount
Oct 11 – 18
Apartment in Northampton
4.95 out of 5 average rating, 281 reviewsBike Path Hideaway Near Smith, Cooley, Northampton
Sep 18 – 25
Apartment in Adams
4.85 out of 5 average rating, 123 reviewsfull apartment in adams and self check in
Jul 15 – 22
Apartment in Bennington
4.93 out of 5 average rating, 529 reviewsThe Octopus's Garden
Jun 18 – 25
Apartment in Greenfield
4.96 out of 5 average rating, 270 reviewsMohawk Trail View/ private apt. no cleaning Fee
Jul 3 – 10
Kid-friendly condo rentals
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
Sep 22 – 29
Condo in North Adams
4.91 out of 5 average rating, 209 reviewsDowntown Flat Iron Condo - walk to MoCA #12
May 9 – 16
Condo in Hudson
4.94 out of 5 average rating, 142 reviewsHarmony Valley Home, bright & inviting 2-BR escape
Apr 16 – 23
Condo in West Dover
4.94 out of 5 average rating, 181 reviewsComfy Condo - 2 Min Walk to Carinthia Grommet Lift
Jul 19 – 26
Condo in Brattleboro
4.92 out of 5 average rating, 286 reviewsPrivate & Quiet Studio Apt. in Vermont
Aug 27 – Sep 3
Condo in Saratoga Springs
4.98 out of 5 average rating, 135 reviewsOwl's Nest - Unique Condo in Vintage Location
Dec 12 – 19
Condo in Albany
4.89 out of 5 average rating, 162 reviewsElegant, spacious studio apt in historic mansion
Jan 4 – 11
Condo in Stratton
4.94 out of 5 average rating, 138 reviewsUpdated Ski in/Ski out Stratton Condo!
Jun 12 – 19
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
G$10,451 GYD before taxes and fees
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