Kid-friendly accommodation & holiday 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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Pittsfield kid-friendly rentals
Child-friendly house rentals
Home in Lee
4.89 out of 5 average rating, 236 reviewsCozy Berkshires Cottage
10 – 17 Oct
Home in Chester
4.96 out of 5 average rating, 312 reviewsRiverfront Getaway
8 – 15 Dec
Home in Pittsfield
4.98 out of 5 average rating, 102 reviewsHidden Oasis in the Mountains by Evergreen Home
9 – 16 Jan
Home in Lee
5.0 out of 5 average rating, 234 reviewsBerkshire Mountain retreat with Urban eco-luxuries
24 Apr – 1 May
Home in Dalton
4.99 out of 5 average rating, 121 reviewsCleveland House - renovated Berkshires' gem.
2 – 9 Feb
Home in Monterey
4.93 out of 5 average rating, 116 reviewsPerfect Berkshire getaway.Cozy cottage.Great wifi.
5 – 12 Sept
Home in Dalton
4.92 out of 5 average rating, 171 reviewsBrooksong, the perfect Berkshires getaway
6 – 13 Jan
Home in Chatham
4.9 out of 5 average rating, 145 reviews2BR Chatham Vlg Home Wi-fi Park@Door Keyless 55"TV
16 – 23 Aug
Kid-Friendly apartment rentals
Apartment in Lee
4.79 out of 5 average rating, 107 reviewsCozy Berkshire Cottage Style Apartment
23 – 30 Apr
Apartment in Great Barrington
4.95 out of 5 average rating, 318 reviewsPrivate En Suite in Beautiful Victorian
21 – 28 Oct
Apartment in North Adams
4.96 out of 5 average rating, 425 reviewsSteps to MoCA, 2bd + SAUNA!
12 – 19 Apr
Apartment in Copake Falls
4.93 out of 5 average rating, 261 reviewsModern Copake Falls Getaway - 8 Mins to Catamount
26 Oct – 2 Nov
Apartment in Northampton
4.95 out of 5 average rating, 281 reviewsBike Path Hideaway Near Smith, Cooley, Northampton
15 – 22 Oct
Apartment in Bennington
4.93 out of 5 average rating, 529 reviewsThe Octopus's Garden
29 July – 5 Aug
Apartment in Shelburne Falls
4.98 out of 5 average rating, 489 reviewsIn town, newly renovated studio with private deck
31 Mar – 7 Apr
Apartment in Adams
4.85 out of 5 average rating, 123 reviewsfull apartment in adams and self check in
21 – 28 July
Child-Friendly Holiday Condos
Condo in North Adams
4.91 out of 5 average rating, 210 reviewsDowntown Flat Iron Condo - walk to MoCA #12
5 – 12 June
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
8 – 15 June
Condo in Hudson
4.94 out of 5 average rating, 143 reviewsHarmony Valley Home, bright & inviting 2-BR escape
14 – 21 Jan
Condo in West Dover
4.94 out of 5 average rating, 181 reviewsComfy Condo - 2 Min Walk to Carinthia Grommet Lift
21 – 28 Sept
Condo in Albany
4.89 out of 5 average rating, 163 reviewsElegant, spacious studio apt in historic mansion
5 – 12 Jan
Condo in Brattleboro
4.92 out of 5 average rating, 286 reviewsPrivate & Quiet Studio Apt. in Vermont
26 Oct – 2 Nov
Condo in Stratton
4.96 out of 5 average rating, 118 reviewsCozy condo within walking distance to the slopes.
28 June – 5 July
Condo in Saratoga Springs
4.98 out of 5 average rating, 135 reviewsOwl's Nest - Unique Condo in Vintage Location
6 – 13 Nov
Quick stats about accommodation & holiday 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
$76 AUD before taxes and fees
Destinations to explore
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