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
Cantabile life in the Berkshires
3 bedrooms
,
·
5 beds
,
·
2 private bathrooms
23–28 Aug
23–28 Aug
$1,969 SGD
Show price breakdown
for 5 nights
$1,969 SGD for 5 nights
,
·
4.95 out of 5 average rating, 217 reviews
4.95 (217)
Top 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
$596 SGD
Show price breakdown
for 5 nights
$596 SGD for 5 nights
5.0 out of 5 average rating, 17 reviews
5.0 (17)
Guest favourite
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed
1 bed
,
·
2 bathrooms
2 bathrooms
23–28 Aug
23–28 Aug
$596 SGD
Show price breakdown
for 5 nights
$596 SGD for 5 nights
4.92 out of 5 average rating, 48 reviews
4.92 (48)
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 Aug
24–29 Aug
$853 SGD
Show price breakdown
for 5 nights
$853 SGD for 5 nights
5.0 out of 5 average rating, 85 reviews
5.0 (85)
Home in Pittsfield
Cozy Berkshire Lakeside Retreat | Deck + Fire Pit
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
10–15 Aug
10–15 Aug
$2,434 SGD
Show price breakdown
for 5 nights
$2,434 SGD for 5 nights
5.0 out of 5 average rating, 4 reviews
5.0 (4)
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
27 Aug – 1 Sept
27 Aug – 1 Sept
$3,441 SGD
Show price breakdown
for 5 nights
$3,441 SGD for 5 nights
5.0 out of 5 average rating, 25 reviews
5.0 (25)
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
$1,290 SGD
Show price breakdown
for 5 nights
$1,290 SGD for 5 nights
4.91 out of 5 average rating, 316 reviews
4.91 (316)
Top guest favourite
Guest favourite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
1.5 bathrooms
1.5 bathrooms
10–15 Jul
10–15 Jul
$2,670 SGD
Show price breakdown
for 5 nights
$2,670 SGD for 5 nights
5.0 out of 5 average rating, 41 reviews
5.0 (41)
Room in Pittsfield
The Yellow Room
1 double bed
1 double bed
,
·
1.5 bathrooms
1.5 bathrooms
12–17 Jul
12–17 Jul
$504 SGD
Show price breakdown
for 5 nights
$504 SGD for 5 nights
4.84 out of 5 average rating, 87 reviews
4.84 (87)
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
22–27 Aug
22–27 Aug
$980 SGD
Show price breakdown
for 5 nights
$980 SGD for 5 nights
4.98 out of 5 average rating, 457 reviews
4.98 (457)
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
$602 SGD
Show price breakdown
for 5 nights
$602 SGD for 5 nights
4.84 out of 5 average rating, 194 reviews
4.84 (194)
Top guest favourite
Guest favourite
Home in New Lebanon
Modernized 1860s Getaway w/ Queechy Lake Passes*
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
26–31 Aug
26–31 Aug
$3,102 SGD
Show price breakdown
for 5 nights
$3,102 SGD for 5 nights
5.0 out of 5 average rating, 16 reviews
5.0 (16)
Guest favourite
Guest favourite
Home in Lenox
Cozy Home in Lenox
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
10–15 Jul
10–15 Jul
$2,202 SGD
Show price breakdown
for 5 nights
$2,202 SGD for 5 nights
5.0 out of 5 average rating, 7 reviews
5.0 (7)
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
23–28 Aug
23–28 Aug
$1,192 SGD
Show price breakdown
for 5 nights
$1,192 SGD for 5 nights
4.99 out of 5 average rating, 314 reviews
4.99 (314)
Guest favourite
Guest favourite
Home in Pittsfield
A Ray of Sunshine-Lakefront-New Construction- ski
5 bedrooms
5 bedrooms
,
·
4.5 bathrooms
4.5 bathrooms
26–31 Jul
26–31 Jul
$7,430 SGD
Show price breakdown
for 5 nights
$7,430 SGD for 5 nights
5.0 out of 5 average rating, 35 reviews
5.0 (35)
Top guest favourite
Guest favourite
Flat in Great Barrington
King Bed |Wi-Fi| 2m to Ski Resort
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
22–27 Aug
22–27 Aug
$1,004 SGD
$910 SGD
Show price breakdown
for 5 nights
4.92 out of 5 average rating, 204 reviews
4.92 (204)
Guest favourite
Guest favourite
Resort in Hancock
Country Inn Suite at Jiminy Peak - No fees added
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
10–15 Jul
10–15 Jul
$1,183 SGD
Show price breakdown
for 5 nights
$1,183 SGD for 5 nights
4.72 out of 5 average rating, 266 reviews
4.72 (266)
Hotel in Lenox
Standard Queen at Hideaway Inn Lenox
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
12–17 Jul
12–17 Jul
$1,222 SGD
Show price breakdown
for 5 nights
$1,222 SGD for 5 nights
New place to stay
New
Guest favourite
Guest favourite
Home in Pittsfield
The Guest House at Cottage Farm
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
3 bathrooms
3 bathrooms
12–17 Jul
12–17 Jul
$2,514 SGD
$2,059 SGD
Show price breakdown
for 5 nights
4.94 out of 5 average rating, 35 reviews
4.94 (35)
1
2
3
4
…
15
