Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
NEW
NEW
Experiences
Experiences, new
NEW
NEW
Services
Services, new
Start your search
Location
Homes in Pittsfield
Check in / Check out
Any week
Guests
Add guests
Filters
0
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
Show map
Search results; Over 1,000 homes in Pittsfield
Over 1,000 homes in Pittsfield
Top guest favourite
Guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom
,
·
1 bed
,
·
1 private bathroom
23–28 Aug
23–28 Aug
$1,215 SGD
Show price breakdown
for 5 nights
$1,215 SGD for 5 nights
,
·
4.99 out of 5 average rating, 310 reviews
4.99 (310)
Guest favourite
Guest favourite
14
Reviews
5.0
Stars
Rating
2
Years hosting
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds
2 beds
12–17 Jul
12–17 Jul
$584 SGD
$432 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 14 reviews
5.0 (14)
Guest favourite
Guest favourite
Flat in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
1–6 Nov
1–6 Nov
$603 SGD
Show price breakdown
for 5 nights
$603 SGD for 5 nights
Pay $0 today
Free cancellation
4.84 out of 5 average rating, 194 reviews
4.84 (194)
Top guest favourite
Guest favourite
82
Reviews
5.0
Stars
Rating
5
Years hosting
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
1 queen bed
1 queen bed
24–29 Aug
24–29 Aug
$855 SGD
Show price breakdown
for 5 nights
$855 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 82 reviews
5.0 (82)
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom
1 bedroom
,
·
2 beds
2 beds
5–10 Jul
5–10 Jul
$1,249 SGD
$883 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
4.64 out of 5 average rating, 28 reviews
4.64 (28)
Top guest favourite
Guest favourite
456
Reviews
4.98
Stars
Rating
9
Years hosting
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
2 beds
2 beds
23–28 Aug
23–28 Aug
$1,015 SGD
Show price breakdown
for 5 nights
$1,015 SGD for 5 nights
Pay $0 today
Free cancellation
4.98 out of 5 average rating, 456 reviews
4.98 (456)
Guest favourite
Guest favourite
30
Reviews
4.77
Stars
Rating
2
Years hosting
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed
1 bed
5–10 Jul
5–10 Jul
$709 SGD
$530 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
4.77 out of 5 average rating, 30 reviews
4.77 (30)
Top guest favourite
Guest favourite
47
Reviews
4.94
Stars
Rating
2
Years hosting
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed
1 bed
23–28 Aug
23–28 Aug
$611 SGD
Show price breakdown
for 5 nights
$611 SGD for 5 nights
Pay $0 today
Free cancellation
4.94 out of 5 average rating, 47 reviews
4.94 (47)
85
Reviews
4.84
Stars
Rating
4
Years hosting
Room in Pittsfield
The Yellow Room
1 double bed
1 double bed
27 Jul – 1 Aug
27 Jul – 1 Aug
$507 SGD
Show price breakdown
for 5 nights
$507 SGD for 5 nights
Pay $0 today
Free cancellation
4.84 out of 5 average rating, 85 reviews
4.84 (85)
Guest favourite
Guest favourite
Home in Pittsfield
Elmer Estate
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
21–26 Oct
21–26 Oct
$1,349 SGD
Show price breakdown
for 5 nights
$1,349 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Guest favourite
Guest favourite
Home in Pittsfield
The Guest House at Cottage Farm
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
12–17 Jul
12–17 Jul
$2,518 SGD
$2,153 SGD
Show price breakdown
for 5 nights
Free cancellation
4.94 out of 5 average rating, 35 reviews
4.94 (35)
Guest favourite
Guest favourite
Guest suite in Pittsfield
Newly Renovated Red Door Annex
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
23–28 Aug
23–28 Aug
$824 SGD
Show price breakdown
for 5 nights
$824 SGD for 5 nights
Pay $0 today
Free cancellation
4.92 out of 5 average rating, 120 reviews
4.92 (120)
Top guest favourite
Guest favourite
Home in Lanesborough
The Pond House
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
9–14 Dec
9–14 Dec
$1,880 SGD
Show price breakdown
for 5 nights
$1,880 SGD for 5 nights
Pay $0 today
Free cancellation
4.96 out of 5 average rating, 49 reviews
4.96 (49)
Top guest favourite
Guest favourite
Flat in Pittsfield
Downtown Apartment A
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
7–12 Sept
7–12 Sept
$1,168 SGD
Show price breakdown
for 5 nights
$1,168 SGD for 5 nights
Pay $0 today
Free cancellation
4.93 out of 5 average rating, 104 reviews
4.93 (104)
Guest favourite
Guest favourite
Guest suite in Hancock
Cozy apartment near Jiminy Peak
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
6–11 Jul
6–11 Jul
$707 SGD
Show price breakdown
for 5 nights
$707 SGD for 5 nights
4.82 out of 5 average rating, 207 reviews
4.82 (207)
Top guest favourite
Guest favourite
197
Reviews
4.96
Stars
Rating
7
Years hosting
Rooms in Pittsfield
Equestrian retreat
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
23–28 Aug
23–28 Aug
$840 SGD
Show price breakdown
for 5 nights
$840 SGD for 5 nights
Pay $0 today
Free cancellation
4.96 out of 5 average rating, 197 reviews
4.96 (197)
Guest favourite
Guest favourite
Home in Pittsfield
Beautiful Lake-view Getaway!
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
5–10 Nov
5–10 Nov
$1,432 SGD
Show price breakdown
for 5 nights
$1,432 SGD for 5 nights
4.97 out of 5 average rating, 66 reviews
4.97 (66)
Guest favourite
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
6–11 Jul
6–11 Jul
$2,494 SGD
$2,287 SGD
Show price breakdown
for 5 nights
4.95 out of 5 average rating, 214 reviews
4.95 (214)
Guest favourite
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
6–11 Jul
6–11 Jul
$1,322 SGD
Show price breakdown
for 5 nights
$1,322 SGD for 5 nights
4.91 out of 5 average rating, 315 reviews
4.91 (315)
1
2
3
4
…
15