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Holiday hires 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 day to stay in a vacation rental in Pittsfield?

The cheapest day to stay in Pittsfield is Sunday ($210). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is $681.

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Other accommodations in Pittsfield

Find the perfect holiday rental for your stay in Pittsfield. There are 56 hotels in Pittsfield and price data was last updated on 21 January 2026. The average price for a hotel in Pittsfield is .
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
$206
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
$107
Avg. per night
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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
$123
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
$133
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 21 January 2026.
Utilise the map to find properties close to the Pittsfield area(s) or attractions you plan on visiting. Clicking a property's name will unlock more information and allow you to book that particular holiday rental.

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 21 January 2026.

  • How much does a holiday rental in Pittsfield cost?

    $343 per night is how much a holiday rental in Pittsfield costs, on average. $123 per night was the cheapest price recently found by our users, though anything for $333 per night or less is a good deal. Keep in mind that Pittsfield holiday rental prices fluctuate throughout the year: the most expensive month to book is July, and the cheapest time to book is January.

  • Are there any Motel holiday rentals in Pittsfield?

    If you’re looking to book a Motel holiday rental in Pittsfield, then you have 5 to choose from. We recommend looking at Heart OF The Berkshires Motel as it’s currently the most popular Motel rental among our users.

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