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Vacation rentals in Pittsfield

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Travel insights for holiday rentals in Pittsfield

Use these up-to-date, data-driven insights about booking a holiday rental in Pittsfield including ideal times to book, pricing trends, and more.

What is the cheapest month to book a vacation rental in Pittsfield?

The cheapest month to book a vacation rental in Pittsfield is April (S$ 156). Conversely, the most expensive month to stay in Pittsfield is July (S$ 647).

What is the cheapest day to stay in a vacation rental in Pittsfield?

The cheapest day to stay in Pittsfield is Tuesday (S$ 172). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is S$ 605.

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Other accommodations in Pittsfield

Find the perfect holiday rental for your stay in Pittsfield. There are 57 hotels in Pittsfield and price data was last updated on 14 March 2026. The average price for a hotel in Pittsfield is S$ 279/night.
Berkshire Inn
Berkshire Inn

Berkshire Inn

150 West Housatonic Street, Pittsfield, MA, United States
1.6 km from city centre
Free Wi-Fi
Air conditioning
S$ 117
Avg. per night
View Deal
Hotel on North
Hotel on North

Hotel on North

297 North Street, Pittsfield, MA, United States
0.7 km from city centre
Free Wi-Fi
Parking
S$ 178
Avg. per night
View Deal
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

1350 West Housatonic Street, Pittsfield, MA, United States
5.7 km from city centre
Free Wi-Fi
Parking
S$ 131
Avg. per night
View Deal
Fairbridge Inn Express Pittsfield
Fairbridge Inn Express Pittsfield

Fairbridge Inn Express Pittsfield

16 Cheshire Road, Pittsfield, MA, United States
4.1 km from city centre
Free Wi-Fi
S$ 101
Avg. per night
View Deal
Heart OF The Berkshires Motel
Heart OF The Berkshires Motel

Heart OF The Berkshires Motel

970 West Housatonic Street, Pittsfield, MA, United States
4.6 km from city centre
Free Wi-Fi
Parking
S$ 122
Avg. per night
View Deal

Where to stay in Pittsfield

Explore different neighbourhoods and areas within Pittsfield to find the perfect location for your stay. Map data was last updated on 14 March 2026.
Utilize the map to find properties close to the Pittsfield area(s) or attractions you plan on visiting. More information on a given vacation rental can be accessed by clicking the vacation rental's name within the map.

Facts about staying in Pittsfield

Find useful tips and insights about staying in Pittsfield to help you make the most of your experience. FAQs were last updated on 14 March 2026.

  • How much does a holiday rental in Pittsfield cost?

    On average, it costs S$ 279 per night for a Pittsfield holiday rental, but S$ 272 per night or less would be considered a good deal. The cheapest holiday rental price our users have found recently in Pittsfield was for S$ 106 per night. If you can, try to avoid booking your rental July (as this is the most expensive month). Booking January (the cheapest month) may end up saving you money.

  • Are there any Motel holiday rentals in Pittsfield?

    There are 5 holiday rentals in Pittsfield that fall under the Motel category, the most popular is Heart OF The Berkshires Motel.

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