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
Top guest favourite
Guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
1 bedroom
,
·
2 beds
,
·
1 private bathroom
23–28 Aug
23–28 Aug
$1,017 SGD
Show price breakdown
for 5 nights
$1,017 SGD for 5 nights
,
·
4.98 out of 5 average rating, 455 reviews
4.98 (455)
Guest favourite
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds
2 beds
,
·
3 bathrooms
3 bathrooms
12–17 Jul
12–17 Jul
$612 SGD
Show price breakdown
for 5 nights
$612 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 14 reviews
5.0 (14)
Home in Pittsfield
Cozy Berkshire Lakeside Retreat | Deck + Fire Pit
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$2,439 SGD
Show price breakdown
for 5 nights
$2,439 SGD for 5 nights
Free cancellation
New place to stay
New
Top guest favourite
Guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
7–12 Jul
7–12 Jul
$3,181 SGD
Show price breakdown
for 5 nights
$3,181 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 24 reviews
5.0 (24)
Home in Pittsfield
Four Seasons Retreat
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
6–11 Jul
6–11 Jul
$1,921 SGD
$1,582 SGD
Show price breakdown
for 5 nights
Free cancellation
4.74 out of 5 average rating, 31 reviews
4.74 (31)
Flat in Pittsfield
Petite Paris
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1.5 bathrooms
1.5 bathrooms
5–10 Jul
5–10 Jul
$1,203 SGD
Show price breakdown
for 5 nights
$1,203 SGD for 5 nights
Free cancellation
4.81 out of 5 average rating, 37 reviews
4.81 (37)
Guest favourite
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed
1 bed
,
·
2 bathrooms
2 bathrooms
12–17 Jul
12–17 Jul
$612 SGD
Show price breakdown
for 5 nights
$612 SGD for 5 nights
Free cancellation
4.94 out of 5 average rating, 47 reviews
4.94 (47)
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
1–6 Jul
1–6 Jul
$1,758 SGD
$1,238 SGD
Show price breakdown
for 5 nights
Free cancellation
4.65 out of 5 average rating, 26 reviews
4.65 (26)
Guest favourite
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
6–11 Jul
6–11 Jul
$2,114 SGD
Show price breakdown
for 5 nights
$2,114 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 214 reviews
4.95 (214)
Room in Pittsfield
The Yellow Room
1 double bed
1 double bed
,
·
1.5 bathrooms
1.5 bathrooms
25–30 Jul
25–30 Jul
$513 SGD
Show price breakdown
for 5 nights
$513 SGD for 5 nights
Free cancellation
4.84 out of 5 average rating, 85 reviews
4.84 (85)
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
$607 SGD
Show price breakdown
for 5 nights
$607 SGD for 5 nights
Free cancellation
4.84 out of 5 average rating, 194 reviews
4.84 (194)
Guest favourite
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed
1 bed
,
·
2 bathrooms
2 bathrooms
1–6 Aug
1–6 Aug
$788 SGD
Show price breakdown
for 5 nights
$788 SGD for 5 nights
Free cancellation
4.77 out of 5 average rating, 30 reviews
4.77 (30)
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 Jul
6–11 Jul
$1,324 SGD
Show price breakdown
for 5 nights
$1,324 SGD for 5 nights
Free cancellation
4.91 out of 5 average rating, 312 reviews
4.91 (312)
Top guest favourite
Guest favourite
Home in Pittsfield
Mountain Farmhouse Getaway
5 bedrooms
5 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
1–6 Jul
1–6 Jul
$3,799 SGD
Show price breakdown
for 5 nights
$3,799 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 23 reviews
5.0 (23)
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
19–24 Jul
19–24 Jul
$849 SGD
Show price breakdown
for 5 nights
$849 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 80 reviews
5.0 (80)
Guest favourite
Guest favourite
Home in Pittsfield
Berkshire Getaway Ranch 3 acres + saltwater pool
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
1–6 Jul
1–6 Jul
$6,032 SGD
Show price breakdown
for 5 nights
$6,032 SGD for 5 nights
Free cancellation
4.92 out of 5 average rating, 103 reviews
4.92 (103)
Home in New Lebanon
Above the Clouds Mountain Retreat
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
4 bathrooms
4 bathrooms
6–11 Jul
6–11 Jul
$3,402 SGD
Show price breakdown
for 5 nights
$3,402 SGD for 5 nights
Free cancellation
New place to stay
New
Top guest favourite
Guest favourite
Home in Pittsfield
Elmer Estate
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
22–27 Sept
22–27 Sept
$1,347 SGD
Show price breakdown
for 5 nights
$1,347 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Guest favourite
Guest favourite
Home in Lenox
Cozy Home in Lenox
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
6–11 Jul
6–11 Jul
$2,197 SGD
Show price breakdown
for 5 nights
$2,197 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 7 reviews
5.0 (7)
1
2
3
4
…
15
