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
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
Guest favourite
Guest favourite
Home in Pittsfield
The Guest House at Cottage Farm
3 bedrooms
,
·
4 beds
,
·
3 private bathrooms
24–29 Aug
24–29 Aug
$2,994 SGD
$2,639 SGD
Show price breakdown
for 5 nights
,
·
4.95 out of 5 average rating, 38 reviews
4.95 (38)
Guest favourite
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds
2 beds
,
·
3 bathrooms
3 bathrooms
30 Aug – 4 Sept
30 Aug – 4 Sept
$590 SGD
Show price breakdown
for 5 nights
$590 SGD for 5 nights
4.86 out of 5 average rating, 28 reviews
4.86 (28)
Superhost
Superhost
Room in Pittsfield
Cozy Corner Room in Downtown Victorian
1 bed
1 bed
,
·
2.5 bathrooms
2.5 bathrooms
14–19 Sept
14–19 Sept
$394 SGD
Show price breakdown
for 5 nights
$394 SGD for 5 nights
Room in Pittsfield
The Yellow Room
1 double bed
1 double bed
,
·
1.5 bathrooms
1.5 bathrooms
29 Aug – 3 Sept
29 Aug – 3 Sept
$527 SGD
Show price breakdown
for 5 nights
$527 SGD for 5 nights
4.84 out of 5 average rating, 90 reviews
4.84 (90)
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
24–29 Sept
24–29 Sept
$831 SGD
Show price breakdown
for 5 nights
$831 SGD for 5 nights
5.0 out of 5 average rating, 88 reviews
5.0 (88)
Guest favourite
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
9–14 Aug
9–14 Aug
$2,256 SGD
$1,847 SGD
Show price breakdown
for 5 nights
4.96 out of 5 average rating, 225 reviews
4.96 (225)
Guest favourite
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed
1 bed
,
·
2 bathrooms
2 bathrooms
6–11 Sept
6–11 Sept
$712 SGD
Show price breakdown
for 5 nights
$712 SGD for 5 nights
4.83 out of 5 average rating, 40 reviews
4.83 (40)
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
$584 SGD
Show price breakdown
for 5 nights
$584 SGD for 5 nights
4.84 out of 5 average rating, 194 reviews
4.84 (194)
Superhost
Superhost
Room in Pittsfield
Sunny Room in Downtown Victorian
1 bed
1 bed
,
·
2 bathrooms
2 bathrooms
17–22 Aug
17–22 Aug
$614 SGD
$434 SGD
Show price breakdown
for 5 nights
4.75 out of 5 average rating, 20 reviews
4.75 (20)
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
23–28 Aug
23–28 Aug
$850 SGD
Show price breakdown
for 5 nights
$850 SGD for 5 nights
4.98 out of 5 average rating, 464 reviews
4.98 (464)
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
$1,089 SGD
Show price breakdown
for 5 nights
$1,089 SGD for 5 nights
4.99 out of 5 average rating, 325 reviews
4.99 (325)
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
22–27 Aug
22–27 Aug
$1,414 SGD
$997 SGD
Show price breakdown
for 5 nights
Extended stay discount
4.65 out of 5 average rating, 43 reviews
4.65 (43)
Top guest favourite
Guest favourite
Room in North Chatham
Charming Eyebrow Colonial North Chatham, NY
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
30 Aug – 4 Sept
30 Aug – 4 Sept
$1,024 SGD
Show price breakdown
for 5 nights
$1,024 SGD for 5 nights
4.97 out of 5 average rating, 614 reviews
4.97 (614)
Guest favourite
Guest favourite
Farm stay in New Lebanon
NEW RENO - Chalet-style farm loft near Tanglewood
1 bedroom
1 bedroom
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
9–14 Aug
9–14 Aug
$1,601 SGD
$727 SGD
Show price breakdown
for 5 nights
4.91 out of 5 average rating, 70 reviews
4.91 (70)
Top guest favourite
Guest favourite
Room in Becket
East b.r. in upstairs suite of open plan home
1 bathroom
1 bathroom
9–14 Aug
9–14 Aug
$566 SGD
Show price breakdown
for 5 nights
$566 SGD for 5 nights
4.87 out of 5 average rating, 259 reviews
4.87 (259)
Top guest favourite
Guest favourite
Room in Pittsfield
Pittsfield. Large queen bedroom, second floor.
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
9–14 Aug
9–14 Aug
$1,062 SGD
$934 SGD
Show price breakdown
for 5 nights
4.96 out of 5 average rating, 48 reviews
4.96 (48)
Guest favourite
Guest favourite
Guest suite in Hancock
Cozy apartment near Jiminy Peak
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
8–13 Sept
8–13 Sept
$705 SGD
Show price breakdown
for 5 nights
$705 SGD for 5 nights
4.81 out of 5 average rating, 209 reviews
4.81 (209)
Top guest favourite
Guest favourite
Flat in New Lebanon
Folk Art Studio: 1-bedroom near the Berkshires
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
5–10 Sept
5–10 Sept
$832 SGD
Show price breakdown
for 5 nights
$832 SGD for 5 nights
5.0 out of 5 average rating, 31 reviews
5.0 (31)
Guest favourite
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
1 bathroom
1 bathroom
9–14 Aug
9–14 Aug
$1,277 SGD
Show price breakdown
for 5 nights
$1,277 SGD for 5 nights
4.92 out of 5 average rating, 322 reviews
4.92 (322)
1
2
3
4
…
15
