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
5.0 out of 5 average rating, 230 reviewsBerkshire Mountain retreat with Urban eco-luxuries
Apr. 19 – 26
Home in Lee
4.89 out of 5 average rating, 235 reviewsCozy Berkshires Cottage
Sep. 13 – 20
Home in Chester
4.96 out of 5 average rating, 311 reviewsRiverfront Getaway
Sep. 6 – 13
Home in Chatham
4.9 out of 5 average rating, 145 reviews2BR Chatham Vlg Home Wi-fi Park@Door Keyless 55"TV
Mar. 22 – 29
Home in Dalton
4.92 out of 5 average rating, 171 reviewsBrooksong, the perfect Berkshires getaway
Dec. 16 – 23
Home in Williamsburg
4.99 out of 5 average rating, 157 reviewsHilltown Studio
Nov. 26 – Dec. 3
Home in Dalton
4.99 out of 5 average rating, 120 reviewsCleveland House - renovated Berkshires' gem.
Sep. 13 – 20
Home in Canaan
4.95 out of 5 average rating, 202 reviewsHudson River Valley/Berkshires
Dec. 6 – 13
Family-friendly apartment rentals
Apartment in Lee
4.78 out of 5 average rating, 106 reviewsCozy Berkshire Cottage Style Apartment
Sep. 4 – 11
Apartment in Great Barrington
4.95 out of 5 average rating, 317 reviewsPrivate En Suite in Beautiful Victorian
Feb. 8 – 15
Apartment in North Adams
4.97 out of 5 average rating, 409 reviewsSee MoCA from your mansion+Sauna! Ski nearby!
Dec. 17 – 24
Apartment in Shelburne Falls
4.98 out of 5 average rating, 488 reviewsIn town, newly renovated studio with private deck
Mar. 14 – 21
Apartment in Bennington
4.93 out of 5 average rating, 527 reviewsThe Octopus's Garden
Oct. 15 – 22
Apartment in Copake Falls
4.93 out of 5 average rating, 258 reviewsModern Copake Falls Getaway - 8 Mins to Catamount
Sep. 13 – 20
Apartment in Adams
4.85 out of 5 average rating, 123 reviewsfull apartment in adams and self check in
Jun. 8 – 15
Apartment in Greenfield
4.96 out of 5 average rating, 269 reviewsMohawk Trail View/ private apt. no cleaning Fee
Jul. 3 – 10
Family-friendly condo rentals
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
May 28 – Jun. 4
Condo in Hudson
4.94 out of 5 average rating, 141 reviewsHarmony Valley Home, bright & inviting 2-BR escape
Oct. 21 – 28
Condo in North Adams
4.91 out of 5 average rating, 209 reviewsDowntown Flat Iron Condo - walk to MoCA #12
May 22 – 29
Condo in Albany
4.89 out of 5 average rating, 161 reviewsElegant, spacious studio apt in historic mansion
Oct. 19 – 26
Condo in Brattleboro
4.92 out of 5 average rating, 284 reviewsPrivate & Quiet Studio Apt. in Vermont
Oct. 5 – 12
Condo in Stratton
4.94 out of 5 average rating, 138 reviewsUpdated Ski in/Ski out Stratton Condo!
Jun. 6 – 13
Condo in West Dover
4.94 out of 5 average rating, 181 reviewsComfy Condo - 2 Min Walk to Carinthia Grommet Lift
Nov. 28 – Dec. 5
Condo in Saratoga Springs
4.98 out of 5 average rating, 134 reviewsOwl's Nest - Unique Condo in Vintage Location
Jan. 8 – 15
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
$68 CAD before taxes and fees
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