Over 1,000 places in Pittsfield

Superhost
Apartment in Pittsfield
Cozy Chic - Studio Apartment
1 queen bed
May 6 – 11
New place to stay
Apartment in Pittsfield
Renovated, Spacious, and Ideal for Families
Apr 19 – 24
4.67 out of 5 average rating, 3 reviews
Apartment in Pittsfield
Beautiful Blue Studio downtown
1 bed
May 3 – 8
5.0 out of 5 average rating, 4 reviews
Guest favorite
Apartment in Pittsfield
Comfortable Pittsfield Loft
1 queen bed
Apr 19 – 24
4.92 out of 5 average rating, 25 reviews
Guest favorite
Room in Dalton
Stay with MaryHosting for 5 years,
Mother in Law unit in Dalton
Apr 19 – 24
4.96 out of 5 average rating, 137 reviews
Guest favorite
Apartment in Pittsfield
Luxury 2BR Apt. Home w/Work Area
2 beds
Apr 24 – 29
4.96 out of 5 average rating, 52 reviews
Room in Pittsfield
Stay with Julia
No Clean Fee! Upper North St Lodge Room
Apr 19 – 24
4.62 out of 5 average rating, 37 reviews
Boutique hotel in Lenox
Standard King in Boutique Lenox Hotel
1 king bed
Apr 19 – 24
4.62 out of 5 average rating, 262 reviews
Guest favorite
Room in Pittsfield
Stay with JosieDigital production,
Large guest suite w/private bath in the Berkshires
Apr 20 – 25
4.99 out of 5 average rating, 374 reviews
Guest favorite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bed
Apr 19 – 24
4.99 out of 5 average rating, 105 reviews
Guest favorite
Home in Pittsfield
Cantabile life in the Berkshires
5 beds
Apr 21 – 26
4.94 out of 5 average rating, 99 reviews
Guest favorite
Home in Pittsfield
Dancing Horse Lodge
6 beds
Apr 21 – 26
4.87 out of 5 average rating, 250 reviews
Guest favorite
Guesthouse in Pittsfield
The Nest at Birdland
4 beds
Apr 19 – 24
4.98 out of 5 average rating, 47 reviews
Guest favorite
Apartment in Pittsfield
Marie's Place
2 queen beds
Apr 19 – 24
4.92 out of 5 average rating, 224 reviews
Guest favorite
Home in Pittsfield
BB's Central Berkshire Home
5 beds
Apr 21 – 26
4.96 out of 5 average rating, 49 reviews
Guest favorite
Cottage in Pittsfield
Cozy Berkshire cottage with indoor fireplace
3 beds
Apr 21 – 26
5.0 out of 5 average rating, 81 reviews
Guest favorite
Home in Pittsfield
Family-Centric Berkshire Getaway by Evergreen Home
4 beds
Apr 21 – 26
4.96 out of 5 average rating, 24 reviews
Guest favorite
Home in Pittsfield
Berkshire Lakefront Home W/Pool-100%Renovated
10 beds
Apr 21 – 26
4.97 out of 5 average rating, 38 reviews