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Holiday rentals 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 ($255). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is $603.

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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 $190 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 27 July 2026
These are the lowest prices we've found on holiday rentals in Pittsfield at the moment. As prices can vary by date, change the dates if you're flexible to compare rates.
Berkshire Mountain Lodge
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Pittsfield, MA, United States
4.4 km from city centre
Air conditioning
$190
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 27 July 2026. The average price for a hotel in Pittsfield is .
Berkshire Inn
Berkshire Inn

Berkshire Inn

150 West Housatonic Street, Pittsfield, MA, United States
1.6 km from city centre
Free Wi-Fi
Parking
$160
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
$190
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
$338
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
$160
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 27 July 2026.
Scroll to and zoom in on the areas in Pittsfield you plan on visiting to find nearby properties. 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 27 July 2026.

  • How much does a holiday rental in Pittsfield cost?

    $363/night is a typical cost for a holiday rental in Pittsfield throughout the year. Rental prices do vary though, and you’ll find that May is the most expensive month to book, and January is the cheapest month to book. HotelsCombined users recently found Pittsfield holiday rentals for as low as $190/night. In general, any Pittsfield rental for $332 or less is a good deal.

  • Are there any Motel holiday rentals in Pittsfield?

    At the moment, there are 5 properties listed as a Motel holiday rental in Pittsfield. A popular Motel in Pittsfield amongst our users is Berkshire Inn.

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