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
Serviced apartment in Pittsfield
One Bedroom Apartment with a full kitchen
1 bedroom
,
·
2 beds
,
·
1 bathroom
6–11 Jul
6–11 Jul
$1,600 SGD
Show price breakdown
for 5 nights
$1,600 SGD for 5 nights
,
·
4.83 out of 5 average rating, 6 reviews
4.83 (6)
Guest favourite
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
5.0 out of 5 average rating, 14 reviews
5.0 (14)
,
·
2 beds
2 beds
,
·
3 bathrooms
3 bathrooms
12–17 Jul
12–17 Jul
$588 SGD
$467 SGD
Show price breakdown
for 5 nights
Free cancellation
Home in Pittsfield
Cozy Berkshire Lakeside Retreat | Deck + Fire Pit
5.0 out of 5 average rating, 3 reviews
5.0 (3)
,
·
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
6–11 Jul
6–11 Jul
$2,501 SGD
Show price breakdown
for 5 nights
$2,501 SGD for 5 nights
Free cancellation
Guest favourite
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
4.95 out of 5 average rating, 214 reviews
4.95 (214)
,
·
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
6–11 Jul
6–11 Jul
$2,278 SGD
$2,071 SGD
Show price breakdown
for 5 nights
Home in Pittsfield
Four Seasons Retreat
4.75 out of 5 average rating, 32 reviews
4.75 (32)
,
·
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
26–31 Jul
26–31 Jul
$1,837 SGD
$1,516 SGD
Show price breakdown
for 5 nights
Top guest favourite
Guest favourite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
5.0 out of 5 average rating, 40 reviews
5.0 (40)
,
·
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
1.5 bathrooms
1.5 bathrooms
8–13 Jul
8–13 Jul
$2,751 SGD
Show price breakdown
for 5 nights
$2,751 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
4.94 out of 5 average rating, 47 reviews
4.94 (47)
,
·
1 bed
1 bed
,
·
2 bathrooms
2 bathrooms
12–17 Jul
12–17 Jul
$588 SGD
$467 SGD
Show price breakdown
for 5 nights
Free cancellation
Room in Pittsfield
The Yellow Room
4.84 out of 5 average rating, 85 reviews
4.84 (85)
,
·
1 double bed
1 double bed
,
·
1.5 bathrooms
1.5 bathrooms
25–30 Jul
25–30 Jul
$508 SGD
Show price breakdown
for 5 nights
$508 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
5.0 out of 5 average rating, 80 reviews
5.0 (80)
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
19–24 Jul
19–24 Jul
$846 SGD
Show price breakdown
for 5 nights
$846 SGD for 5 nights
Top guest favourite
Guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
4.98 out of 5 average rating, 455 reviews
4.98 (455)
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
23–28 Aug
23–28 Aug
$1,014 SGD
Show price breakdown
for 5 nights
$1,014 SGD for 5 nights
Top guest favourite
Guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
5.0 out of 5 average rating, 25 reviews
5.0 (25)
,
·
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
27 Aug – 1 Sept
27 Aug – 1 Sept
$3,536 SGD
Show price breakdown
for 5 nights
$3,536 SGD for 5 nights
Top guest favourite
Guest favourite
Flat in Pittsfield
Downtown Apartment A
4.93 out of 5 average rating, 103 reviews
4.93 (103)
,
·
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
7–12 Sept
7–12 Sept
$1,166 SGD
Show price breakdown
for 5 nights
$1,166 SGD for 5 nights
Top guest favourite
Guest favourite
Home in Pittsfield
Marie’s Place unit 3
4.97 out of 5 average rating, 61 reviews
4.97 (61)
,
·
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1.5 bathrooms
1.5 bathrooms
22–27 Aug
22–27 Aug
$2,050 SGD
Show price breakdown
for 5 nights
$2,050 SGD for 5 nights
Guest favourite
Guest favourite
Flat in Pittsfield
Marie's Place, Unit 1
4.97 out of 5 average rating, 115 reviews
4.97 (115)
,
·
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
4–9 Jul
4–9 Jul
$1,823 SGD
Show price breakdown
for 5 nights
$1,823 SGD for 5 nights
Guest favourite
Guest favourite
Home in Pittsfield
Berkshire Views
5.0 out of 5 average rating, 19 reviews
5.0 (19)
,
·
6 bedrooms
6 bedrooms
,
·
7 beds
7 beds
,
·
4 bathrooms
4 bathrooms
13–18 Sept
13–18 Sept
$4,915 SGD
Show price breakdown
for 5 nights
$4,915 SGD for 5 nights
Guest favourite
Guest favourite
Flat in Pittsfield
Marie's Place
4.91 out of 5 average rating, 314 reviews
4.91 (314)
,
·
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
6–11 Jul
6–11 Jul
$1,320 SGD
Show price breakdown
for 5 nights
$1,320 SGD for 5 nights
Guest favourite
Guest favourite
Home in Pittsfield
The Guest House at Cottage Farm
4.94 out of 5 average rating, 35 reviews
4.94 (35)
,
·
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
3 bathrooms
3 bathrooms
12–17 Jul
12–17 Jul
$2,515 SGD
$2,242 SGD
Show price breakdown
for 5 nights
Home in Pittsfield
Berkshire Estate
4.8 out of 5 average rating, 15 reviews
4.8 (15)
,
·
9 bedrooms
9 bedrooms
,
·
10 beds
10 beds
,
·
4.5 bathrooms
4.5 bathrooms
15–20 Jul
15–20 Jul
$7,238 SGD
Show price breakdown
for 5 nights
$7,238 SGD for 5 nights
Top guest favourite
Guest favourite
Home in Pittsfield
Spacious 4 Br+ house in the heart of Berkshires
4.95 out of 5 average rating, 74 reviews
4.95 (74)
,
·
5 bedrooms
5 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
30 Aug – 4 Sept
30 Aug – 4 Sept
$2,629 SGD
Show price breakdown
for 5 nights
$2,629 SGD for 5 nights
1
2
3
4
…
15