Kid-friendly holiday rentals in Pittsfield
Find and book unique family-friendly rentals on Airbnb
Top-rated family-friendly rentals in Pittsfield
Guests agree: these family-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 family-friendly rentals
Kid-friendly house rentals
Home in Chester
4.96 out of 5 average rating, 312 reviewsRiverfront Getaway
14–21 Oct
Home in Lee
4.89 out of 5 average rating, 236 reviewsCozy Berkshires Cottage
8–15 May
Home in Lee
5.0 out of 5 average rating, 231 reviewsBerkshire Mountain retreat with Urban eco-luxuries
24 Apr – 1 May
Home in Dalton
4.92 out of 5 average rating, 171 reviewsBrooksong, the perfect Berkshires getaway
28 Sep – 5 Oct
Home in Dalton
4.99 out of 5 average rating, 121 reviewsCleveland House - renovated Berkshires' gem.
4–11 Jan
Home in Monterey
4.93 out of 5 average rating, 307 reviewsCharming cottage w/ gorgeous views.
4–11 Jan
Home in Chatham
4.9 out of 5 average rating, 145 reviews2BR Chatham Vlg Home Wi-fi Park@Door Keyless 55"TV
5–12 Dec
Home in Canaan
4.9 out of 5 average rating, 150 reviewsBerkshire Lakefront House with Amazing Views
6–13 Jan
Family-friendly apartment rentals
Flat in Petersburg
4.85 out of 5 average rating, 149 reviewsThe Beer Diviner Brewery Apartment
5–12 Feb
Flat in Pittsfield
4.92 out of 5 average rating, 225 reviewsMarie's Place
11–18 Apr
Flat in Plainfield
4.95 out of 5 average rating, 237 reviewsSunny carriage house apartment
12–19 Aug
Flat in Great Barrington
4.95 out of 5 average rating, 318 reviewsPrivate En Suite in Beautiful Victorian
3–10 Dec
Flat in North Adams
4.97 out of 5 average rating, 411 reviewsSee MoCA from your mansion+Sauna!
14–21 Dec
Flat in Copake Falls
4.93 out of 5 average rating, 260 reviewsModern Copake Falls Getaway - 8 Mins to Catamount
7–14 Oct
Flat in Adams
4.85 out of 5 average rating, 123 reviewsfull apartment in adams and self check in
15–22 Jul
Flat in Bennington
4.93 out of 5 average rating, 529 reviewsThe Octopus's Garden
20–27 Jun
Family-friendly apartment rentals
Apartment in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
19–26 Mar
Apartment in North Adams
4.91 out of 5 average rating, 209 reviewsDowntown Flat Iron Condo - walk to MoCA #12
11–18 Jul
Apartment in Hudson
4.94 out of 5 average rating, 142 reviewsHarmony Valley Home, bright & inviting 2-BR escape
23–30 Dec
Apartment in Albany
4.89 out of 5 average rating, 162 reviewsElegant, spacious studio apt in historic mansion
4–11 Jan
Apartment in West Dover
4.94 out of 5 average rating, 181 reviewsComfy Condo - 2 Min Walk to Carinthia Grommet Lift
4–11 Aug
Apartment in Brattleboro
4.92 out of 5 average rating, 286 reviewsPrivate & Quiet Studio Apt. in Vermont
27 Aug – 3 Sep
Apartment in Stratton
4.96 out of 5 average rating, 118 reviewsCozy condo within walking distance to the slopes.
14–21 Jun
Apartment in Saratoga Springs
4.98 out of 5 average rating, 135 reviewsOwl's Nest - Unique Condo in Vintage Location
12–19 Dec
Quick stats about 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
1.8T reviews
Nightly prices starting at
₹4,170 before taxes and fees
Destinations to explore
- New City Holiday rentals
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