Search results; Over 1,000 homes in Pittsfield

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Guest favorite
Room in Pittsfield
Stay with SusanArtist and musician,
The Yellow Room
Aug 17 – 22
R6,479 ZAR for 5 nights
4.86 out of 5 average rating, 71 reviews
Guest favorite
Guest suite in Pittsfield
Newly Renovated Red Door Annex
1 queen bed
Aug 17 – 22
R11,285 ZAR for 5 nights
4.89 out of 5 average rating, 82 reviews
Guest favorite
Apartment in Pittsfield
Comfortable Pittsfield Loft
1 queen bed
Sep 8 – 13
R8,882 ZAR for 5 nights
4.91 out of 5 average rating, 47 reviews
Superhost
Apartment in Pittsfield
Newly Renovated, and Spacious great for family
1 queen bed
Sep 7 – 12
R7,613 ZAR for 5 nights
4.75 out of 5 average rating, 59 reviews
Room in Pittsfield
Stay with Julia
No Clean Fee! Upper North St Lodge Room
Aug 24 – 29
R6,489 ZAR for 5 nights
4.69 out of 5 average rating, 90 reviews
Top guest favorite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
4 beds
Sep 14 – 19
R35,839 ZAR for 5 nights
5.0 out of 5 average rating, 23 reviews
Top guest favorite
Room in Pittsfield
Stay with JosieDigital production,
Petite space for a getaway
Mar 17 – 22
R8,464 ZAR for 5 nights
5.0 out of 5 average rating, 44 reviews
Top guest favorite
Room in Pittsfield
Stay with JosieDigital production,
Large guest suite w/private bath in the Berkshires
Sep 7 – 12
R9,509 ZAR for 5 nights
4.98 out of 5 average rating, 428 reviews
Apartment in Pittsfield
Beautiful Blue Studio downtown
1 bed
Aug 31 – Sep 5
R7,306 ZAR for 5 nights
4.59 out of 5 average rating, 37 reviews
Guest favorite
Apartment in Pittsfield
Green 2 bedroom Downtown
4 beds
Aug 17 – 22
R12,702 ZAR for 5 nights
4.88 out of 5 average rating, 32 reviews
Room in Pittsfield
Stay with Rachel
Charming Turret Room in Downtown Victorian
Sep 9 – 14
R9,613 ZAR for 5 nights
4.67 out of 5 average rating, 15 reviews
Top guest favorite
Home in Pittsfield
Marie’s Place unit 3
3 beds
Aug 17 – 22
R21,222 ZAR for 5 nights
4.98 out of 5 average rating, 40 reviews
Guest favorite
Room in Dalton
Stay with MaryHosting for 6 years,
Mother in Law unit in Dalton
Sep 2 – 7
R10,261 ZAR for 5 nights
4.95 out of 5 average rating, 155 reviews
Superhost
Room in Pittsfield
Stay with Berkshire Theatre Group
The Artist House - Room 5
Nov 1 – 6
R10,031 ZAR for 5 nights
Home in Pittsfield
Berkshires Getaway: 1BR Near Mount - Forest View
2 beds
Aug 17 – 22
R14,545 ZAR for 5 nights
New place to stay
Superhost
Apartment in Pittsfield
Spacious 2 bedroom downtown
3 beds
Aug 17 – 22
R12,389 ZAR for 5 nights
4.79 out of 5 average rating, 19 reviews
Guest favorite
Home in Pittsfield
Spacious Historic Home in the Berkshires!
5 beds
Aug 31 – Sep 5
R30,667 ZAR for 5 nights
4.87 out of 5 average rating, 15 reviews
Guest favorite
Home in Pittsfield
Whispering Woods Guest House
2 beds
Sep 7 – 12
R16,166 ZAR for 5 nights
4.97 out of 5 average rating, 31 reviews