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Search results; Over 1,000 homes in Pittsfield

Top guest favourite

Guest suite in Pittsfield

Newly Renovated Red Door Annex

1 bedroom, 1 bed, 1 private bathroom

7–12 Sept

$831 SGD for 5 nights

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4.92 out of 5 average rating, 134 reviews

Guest favourite

Home in Pittsfield

Cantabile life in the Berkshires

3 bedrooms, 5 beds

9–14 Aug

4.96 out of 5 average rating, 226 reviews

Top guest favourite

Home in Pittsfield

Cozy cottage on peaceful pond

2 bedrooms, 2 beds

26–31 Oct

$2,601 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 32 reviews

Guest favourite

Room in Pittsfield

Cute Room with Bay Window in Downtown Victorian

2 beds

30 Aug – 4 Sept

$590 SGD for 5 nights

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Free cancellation

4.86 out of 5 average rating, 28 reviews

Guest favourite

Flat in Pittsfield

Marie's Place

2 bedrooms, 2 queen beds

9–14 Aug

$1,277 SGD for 5 nights

4.92 out of 5 average rating, 323 reviews

Hotel room in Pittsfield

1 BD • Berkshires Apartment • Full Kitchen/Pool

1 bedroom, 2 beds

22–27 Aug

Extended stay discount

Pay $0 today

Free cancellation

4.65 out of 5 average rating, 43 reviews

Top guest favourite

Home in Lee

Berkshire Mountain retreat with Urban eco-luxuries

3 bedrooms, 4 beds

20–25 Sept

$2,842 SGD for 5 nights

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Free cancellation

4.99 out of 5 average rating, 312 reviews

Top guest favourite

Home in Pittsfield

Marie’s Place unit 3

3 bedrooms, 3 beds

23–28 Aug

$2,009 SGD for 5 nights

4.97 out of 5 average rating, 70 reviews

Guest favourite

Room in Pittsfield

Blue Suite in Downtown Victorian

1 bed

6–11 Sept

$712 SGD for 5 nights

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Free cancellation

4.83 out of 5 average rating, 40 reviews

Guest favourite

Flat in Pittsfield

HawksNest: quiet 2BR apt, heart of the Berkshires

2 bedrooms, 2 beds

1–6 Nov

$584 SGD for 5 nights

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Free cancellation

4.84 out of 5 average rating, 194 reviews

Guest favourite

Home in Pittsfield

The Guest House at Cottage Farm

3 bedrooms, 4 beds

24–29 Aug

Free cancellation

4.95 out of 5 average rating, 38 reviews

Guest favourite

Flat in Pittsfield

Marie's Place, Unit 1

3 bedrooms, 3 beds

9–14 Aug

$1,751 SGD for 5 nights

4.97 out of 5 average rating, 122 reviews

Top guest favourite

Home in Lanesborough

The Pond House

3 bedrooms, 4 beds

20–25 Nov

$1,858 SGD for 5 nights

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Free cancellation

4.96 out of 5 average rating, 52 reviews

Superhost

Room in Pittsfield

Cozy Corner Room in Downtown Victorian

1 bed

14–19 Sept

$394 SGD for 5 nights

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Free cancellation

Top guest favourite

Home in Pittsfield

Solomon Ely Homestead set in walkable downtown

4 bedrooms, 4 beds

8–13 Sept

$2,805 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 43 reviews

Top guest favourite

Room in Pittsfield

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

1 queen bed

24–29 Sept

$831 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 88 reviews

Guest favourite

Cottage in Lanesborough

Wildlife Lakeside Cottage; views/wildlife

3 bedrooms, 4 beds

5–10 Oct

$2,168 SGD for 5 nights

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Free cancellation

4.85 out of 5 average rating, 297 reviews

Top guest favourite

Farm stay in Pittsfield

Private 2nd-floor studio on a working produce farm

1 bedroom, 1 bed

25–30 Sept

$1,089 SGD for 5 nights

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Free cancellation

4.99 out of 5 average rating, 325 reviews

Guest favourite

Cottage in Lanesborough

Lakefront Cottage w/ Dock & Kayaks

2 bedrooms, 6 beds

14–19 Sept

Extended stay discount

Pay $0 today

Free cancellation

4.9 out of 5 average rating, 10 reviews