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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 day to stay in a vacation rental in Pittsfield?

The cheapest day to stay in Pittsfield is Sunday ($211). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is $500.

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Cheapest holiday rentals in Pittsfield, Massachusetts

Discover affordable stays in Pittsfield that provide a quality experience without breaking the bank. Hotels in Pittsfield can be found for as low as $157 per night. There is currently one property in Pittsfield that can be booked for this price. Berkshire Mountain Lodge is one of the hotels that can be booked for the lowest price in Pittsfield. Price data was last updated on 23 July 2026
At the moment, these holiday rentals offer the lowest nightly rate out of those we've come across in Pittsfield. Consider alternative dates if you're able to compare prices.
Berkshire Mountain Lodge
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Pittsfield, MA, United States
4.4 km from city centre
Air conditioning
$157
Avg. per night
View Deal

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 23 July 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
$280
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
$133
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
Parking
$131
Avg. per night
View Deal
Berkshire Mountain Lodge
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Pittsfield, MA, United States
4.4 km from city centre
Air conditioning
$157
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 23 July 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 23 July 2026.

  • How much does a holiday rental in Pittsfield cost?

    $301 per night is how much a holiday rental in Pittsfield costs, on average. $157 per night was the cheapest price recently found by our users, though anything for $275 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 May, 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 Berkshire Inn as it’s currently the most popular Motel rental among our users.

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