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
Sep 30 – Oct 7
Home in Chester
4.96 out of 5 average rating, 312 reviewsRiverfront Getaway
Nov 7 – 14
Home in Lee
5.0 out of 5 average rating, 232 reviewsBerkshire Mountain retreat with Urban eco-luxuries
Apr 21 – 28
Home in Dalton
4.92 out of 5 average rating, 171 reviewsBrooksong, the perfect Berkshires getaway
Mar 19 – 26
Home in Dalton
4.99 out of 5 average rating, 121 reviewsCleveland House - renovated Berkshires' gem.
Nov 4 – 11
Home in Lee
4.9 out of 5 average rating, 205 reviews1817 Berkshire Farmhouse- Close to Everything.
Sep 30 – Oct 7
Home in Monterey
4.93 out of 5 average rating, 116 reviewsPerfect Berkshire getaway.Cozy cottage.Great wifi.
Sep 6 – 13
Home in Monterey
4.93 out of 5 average rating, 308 reviewsCharming cottage w/ gorgeous views.
Feb 5 – 12
Kid-friendly apartment rentals
Apartment in Lee
4.79 out of 5 average rating, 107 reviewsCozy Berkshire Cottage Style Apartment
Apr 20 – 27
Apartment in Great Barrington
4.95 out of 5 average rating, 318 reviewsPrivate En Suite in Beautiful Victorian
Nov 11 – 18
Apartment in North Adams
4.96 out of 5 average rating, 424 reviewsSteps to MoCA, 2bd + SAUNA!
Feb 15 – 22
Apartment in Copake Falls
4.93 out of 5 average rating, 260 reviewsModern Copake Falls Getaway - 8 Mins to Catamount
Oct 20 – 27
Apartment in Northampton
4.95 out of 5 average rating, 281 reviewsBike Path Hideaway Near Smith, Cooley, Northampton
Sep 1 – 8
Apartment in Bennington
4.93 out of 5 average rating, 529 reviewsThe Octopus's Garden
Jun 19 – 26
Apartment in North Adams
4.91 out of 5 average rating, 113 reviewsCozy 1 bedroom 1/2 mile to MassMoca
Aug 27 – Sep 3
Apartment in Shelburne Falls
4.98 out of 5 average rating, 488 reviewsIn town, newly renovated studio with private deck
Feb 19 – 26
Kid-friendly condo rentals
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
Jun 5 – 12
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, 143 reviewsHarmony Valley Home, bright & inviting 2-BR escape
Jun 19 – 26
Condo in West Dover
4.94 out of 5 average rating, 181 reviewsComfy Condo - 2 Min Walk to Carinthia Grommet Lift
Feb 24 – Mar 3
Condo in Albany
4.89 out of 5 average rating, 162 reviewsElegant, spacious studio apt in historic mansion
Jan 3 – 10
Condo in Brattleboro
4.92 out of 5 average rating, 286 reviewsPrivate & Quiet Studio Apt. in Vermont
Sep 13 – 20
Condo in Saratoga Springs
4.98 out of 5 average rating, 135 reviewsOwl's Nest - Unique Condo in Vintage Location
Dec 8 – 15
Condo in Saratoga Springs
4.98 out of 5 average rating, 213 reviewsBest Location Racing Season, Broadway, The Belmont
Jun 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
$50 before taxes and fees
Destinations to explore
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