Vacation rentals in Pittsfield

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Travel insights for vacation rentals in Pittsfield

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

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

The cheapest day to stay in Pittsfield is Wednesday ($120). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is $366.
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Other accommodations in Pittsfield

Find the perfect vacation rental for your stay in Pittsfield. There are 72 hotels in Pittsfield and price data was last updated on September 11, 2025. The average price for a hotel in Pittsfield is .
Berkshire Inn
Berkshire Inn

Berkshire Inn

150 West Housatonic Street, Pittsfield, MA, United States
1.0 mi from city centre
Free Wi-Fi
Air Conditioning
$103
Avg. per night
View Deal
Hotel on North
Hotel on North

Hotel on North

297 North Street, Pittsfield, MA, United States
0.4 mi from city centre
Free Wi-Fi
Parking
$222
Avg. per night
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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
3.6 mi from city centre
Free Wi-Fi
Parking
$132
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
2.5 mi from city centre
Free Wi-Fi
Parking
$88
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
2.9 mi from city centre
Free Wi-Fi
Parking
$96
Avg. per night
View Deal

Where to stay in Pittsfield

Explore different neighborhoods and areas within Pittsfield to find the perfect location for your stay. Map data was last updated on September 11, 2025.
Scroll through the map to find vacation rentals close to the Pittsfield neighborhood(s) you plan on visiting. Users can click on a vacation rental's name to find more information about it, such as price, reviews, and amenities, and also find different deals for the property.

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 September 11, 2025.

  • How much does a vacation rental in Pittsfield cost?

    $272 per night is how much a vacation rental in Pittsfield costs, on average. $40 per night was the cheapest price recently found by our users, though anything for $254 per night or less is a good deal. Keep in mind that Pittsfield vacation rental prices fluctuate throughout the year: the most expensive month to book is May, and the cheapest time to book is February.

  • Are there any Motel vacation rentals in Pittsfield?

    At the moment, there are 5 properties listed as a Motel vacation rental in Pittsfield. A popular Motel in Pittsfield amongst our users is Heart OF The Berkshires Motel.

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