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Search results; 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

$1,599 SGD for 5 nights

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4.83 out of 5 average rating, 6 reviews

Guest favourite

Room in Pittsfield

Cute Room with Bay Window in Downtown Victorian

2 beds, 3 bathrooms

12–17 Jul

$431 SGD for 5 nights

5.0 out of 5 average rating, 16 reviews

Top guest favourite

Room in Pittsfield

2-Rm Suite in the Berkshires - private BR and Den

1 queen bed, 1 bathroom

24–29 Aug

$853 SGD for 5 nights

5.0 out of 5 average rating, 83 reviews

Guest favourite

Flat in Pittsfield

HawksNest: quiet 2BR apt, heart of the Berkshires

2 bedrooms, 2 beds, 1.5 bathrooms

1–6 Nov

$602 SGD for 5 nights

4.84 out of 5 average rating, 194 reviews

Top guest favourite

Room in Pittsfield

Romantic King Room in Downtown Victorian

1 bed, 2 bathrooms

23–28 Aug

$609 SGD for 5 nights

4.92 out of 5 average rating, 48 reviews

Top guest favourite

Room in Pittsfield

Large guest suite w/private bath in the Berkshires

2 beds, 1 bathroom

23–28 Aug

$1,013 SGD for 5 nights

4.98 out of 5 average rating, 456 reviews

Room in Pittsfield

The Yellow Room

1 double bed, 1.5 bathrooms

27 Jul – 1 Aug

$506 SGD for 5 nights

4.84 out of 5 average rating, 86 reviews

Guest favourite

Home in Pittsfield

The Guest House at Cottage Farm

3 bedrooms, 4 beds, 3 bathrooms

12–17 Jul

$2,058 SGD for 5 nights

4.94 out of 5 average rating, 35 reviews

Top guest favourite

Flat in Pittsfield

Downtown Apartment A

2 bedrooms, 3 beds, 1 bathroom

28 Jul – 2 Aug

$1,195 SGD for 5 nights

4.93 out of 5 average rating, 104 reviews

Guest favourite

Home in Pittsfield

Net Zero home with rustic Berkshire charm

3 bedrooms, 4 beds, 1 bathroom

28 Oct – 2 Nov

$1,168 SGD for 5 nights

4.93 out of 5 average rating, 133 reviews

Top guest favourite

Home in Lanesborough

The Pond House

3 bedrooms, 4 beds, 1 bathroom

9–14 Dec

$1,876 SGD for 5 nights

4.96 out of 5 average rating, 49 reviews

Top guest favourite

Farm stay in Pittsfield

Private 2nd-floor studio on a working produce farm

1 bedroom, 1 bed, 1 bathroom

23–28 Aug

$1,221 SGD for 5 nights

4.99 out of 5 average rating, 311 reviews

Guest favourite

Flat in Pittsfield

Marie's Place

2 bedrooms, 2 queen beds, 1 bathroom

6–11 Jul

$1,319 SGD for 5 nights

4.91 out of 5 average rating, 315 reviews

Guest favourite

Guest suite in Pittsfield

Newly Renovated Red Door Annex

1 bedroom, 1 queen bed, 1 bathroom

23–28 Aug

$822 SGD for 5 nights

4.91 out of 5 average rating, 122 reviews

Guest favourite

Home in Lenox

Cozy Home in Lenox

2 bedrooms, 2 beds, 1 bathroom

6–11 Jul

$2,130 SGD for 5 nights

5.0 out of 5 average rating, 7 reviews

Guest favourite

Home in Pittsfield

Cantabile life in the Berkshires

3 bedrooms, 5 beds, 2 bathrooms

23–28 Aug

$1,968 SGD for 5 nights

4.95 out of 5 average rating, 215 reviews

Guest favourite

Home in Pittsfield

Elmer Estate

3 bedrooms, 3 beds, 1 bathroom

21–26 Oct

$1,332 SGD for 5 nights

5.0 out of 5 average rating, 7 reviews

Top guest favourite

Home in Pittsfield

Solomon Ely Homestead set in walkable downtown

4 bedrooms, 4 beds, 1.5 bathrooms

8–13 Jul

$2,748 SGD for 5 nights

5.0 out of 5 average rating, 41 reviews

Guest favourite

Home in Pittsfield

Beautiful Lake-view Getaway!

2 bedrooms, 2 queen beds, 1 bathroom

5–10 Nov

$1,424 SGD for 5 nights

4.97 out of 5 average rating, 67 reviews