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Holiday hires in Pittsfield

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Travel insights for holiday rentals in Pittsfield

Use our HotelsCombined data-powered tips to help you find your next holiday rental in Pittsfield.

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

The cheapest month to book a vacation rental in Pittsfield is April ($181). Conversely, the most expensive month to stay in Pittsfield is June ($397).

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

The cheapest day to stay in Pittsfield is Thursday ($183). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is $475.

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Other accommodations in Pittsfield

Find the perfect holiday rental for your stay in Pittsfield. There are 54 hotels in Pittsfield and price data was last updated on 21 April 2026. The average price for a hotel in Pittsfield is $263/night.
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
$162
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
$197
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
$123
Avg. per night
View Deal
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
$123
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 April 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 April 2026.

  • How much does a holiday rental in Pittsfield cost?

    $264 per night is how much a holiday rental in Pittsfield costs, on average. $116 per night was the cheapest price recently found by our users, though anything for $248 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 January, 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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