Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
Experiences
Experiences
Services
Services
Start your search
Location
Homes in Pittsfield
Check in / Check out
Any week
Guests
Add guests
Become a host
Help Centre
Become a host
It’s easy to start hosting and earn extra income.
Refer a host
Find a co-host
Log in or sign up
filters
Filters
Price
Type of place
Show map
Search results; Over 1,000 homes in Pittsfield
Over 1,000 homes in Pittsfield
Top guest favourite
Guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms
,
·
2 beds
,
·
1 private bathroom
8–13 Sept
8–13 Sept
$2,754 SGD
Show price breakdown
for 5 nights
$2,754 SGD for 5 nights
,
·
5.0 out of 5 average rating, 37 reviews
5.0 (37)
Guest favourite
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds
2 beds
,
·
3 bathrooms
3 bathrooms
6–11 Sept
6–11 Sept
$586 SGD
$414 SGD
Show price breakdown
for 5 nights
Free cancellation
4.89 out of 5 average rating, 38 reviews
4.89 (38)
Top guest favourite
Guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
2 beds
2 beds
,
·
1 bathroom
1 bathroom
12–17 Sept
12–17 Sept
$814 SGD
$728 SGD
Show price breakdown
for 5 nights
Free cancellation
4.98 out of 5 average rating, 464 reviews
4.98 (464)
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
6–11 Sept
6–11 Sept
$1,162 SGD
$821 SGD
Show price breakdown
for 5 nights
Extended stay discount
Free cancellation
4.66 out of 5 average rating, 47 reviews
4.66 (47)
Guest favourite
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed
1 bed
,
·
2 bathrooms
2 bathrooms
7–12 Sept
7–12 Sept
$610 SGD
$473 SGD
Show price breakdown
for 5 nights
Free cancellation
4.92 out of 5 average rating, 59 reviews
4.92 (59)
Home in Pittsfield
Lake House Onota Lake
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
2–7 Sept
2–7 Sept
$1,758 SGD
Show price breakdown
for 5 nights
$1,758 SGD for 5 nights
Free cancellation
Guest favourite
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed
1 bed
,
·
2 bathrooms
2 bathrooms
7–12 Sept
7–12 Sept
$749 SGD
$566 SGD
Show price breakdown
for 5 nights
Free cancellation
4.84 out of 5 average rating, 45 reviews
4.84 (45)
Top guest favourite
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
11–16 Sept
11–16 Sept
$1,609 SGD
Show price breakdown
for 5 nights
$1,609 SGD for 5 nights
4.96 out of 5 average rating, 230 reviews
4.96 (230)
Guest favourite
Guest favourite
Flat in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1.5 bathrooms
1.5 bathrooms
1–6 Nov
1–6 Nov
$574 SGD
Show price breakdown
for 5 nights
$574 SGD for 5 nights
Free cancellation
4.84 out of 5 average rating, 194 reviews
4.84 (194)
Top guest favourite
Guest favourite
Home in Pittsfield
Spacious 4 Br+ house in the heart of Berkshires
5 bedrooms
5 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
1–6 Sept
1–6 Sept
$2,671 SGD
Show price breakdown
for 5 nights
$2,671 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 75 reviews
4.95 (75)
Top guest favourite
Guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
3–8 Oct
3–8 Oct
$933 SGD
$818 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 93 reviews
5.0 (93)
Guest favourite
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
1 bathroom
1 bathroom
6–11 Sept
6–11 Sept
$1,372 SGD
$1,203 SGD
Show price breakdown
for 5 nights
4.92 out of 5 average rating, 327 reviews
4.92 (327)
Guest favourite
Guest favourite
Home in Pittsfield
Net Zero home with rustic Berkshire charm
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
28 Oct – 2 Nov
28 Oct – 2 Nov
$1,078 SGD
Show price breakdown
for 5 nights
$1,078 SGD for 5 nights
Free cancellation
4.93 out of 5 average rating, 133 reviews
4.93 (133)
Top guest favourite
Guest favourite
Guest suite in Pittsfield
Newly Renovated Red Door Annex
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
12–17 Sept
12–17 Sept
$824 SGD
Show price breakdown
for 5 nights
$824 SGD for 5 nights
Free cancellation
4.92 out of 5 average rating, 139 reviews
4.92 (139)
Top guest favourite
Guest favourite
Home in Pittsfield
Lakefront home in the heart of the Berkshires
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
4 bathrooms
4 bathrooms
1–6 Sept
1–6 Sept
$4,938 SGD
Show price breakdown
for 5 nights
$4,938 SGD for 5 nights
Free cancellation
4.94 out of 5 average rating, 47 reviews
4.94 (47)
Top guest favourite
Guest favourite
Home in Pittsfield
Charming Historic Retreat, <15 min from Lenox
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
2.5 bathrooms
2.5 bathrooms
8–13 Sept
8–13 Sept
$4,414 SGD
Show price breakdown
for 5 nights
$4,414 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 14 reviews
5.0 (14)
Guest favourite
Guest favourite
Home in Pittsfield
Beautiful Lake-view Getaway!
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
1 bathroom
1 bathroom
8–13 Sept
8–13 Sept
$1,628 SGD
Show price breakdown
for 5 nights
$1,628 SGD for 5 nights
4.97 out of 5 average rating, 73 reviews
4.97 (73)
Room in Pittsfield
The Yellow Room
1 double bed
1 double bed
,
·
1.5 bathrooms
1.5 bathrooms
12–17 Oct
12–17 Oct
$587 SGD
$520 SGD
Show price breakdown
for 5 nights
Free cancellation
4.83 out of 5 average rating, 95 reviews
4.83 (95)
Top guest favourite
Guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
25–30 Sept
25–30 Sept
$1,035 SGD
Show price breakdown
for 5 nights
$1,035 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 329 reviews
4.99 (329)
1
2
3
4
…
15