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Vacation 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 (S$ 191). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is S$ 424.

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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 S$ 142 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 30 July 2026
At the moment, these vacation 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
S$ 142
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 30 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
S$ 258
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
S$ 120
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
S$ 142
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
S$ 119
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 30 July 2026.
Utilize the map to find properties close to the Pittsfield area(s) or attractions you plan on visiting. More information on a given vacation rental can be accessed by clicking the vacation rental's name within the map.

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 30 July 2026.

  • How much does a holiday rental in Pittsfield cost?

    On average, it costs S$ 291 per night for a Pittsfield holiday rental, but S$ 239 per night or less would be considered a good deal. The cheapest holiday rental price our users have found recently in Pittsfield was for S$ 142 per night. If you can, try to avoid booking your rental May (as this is the most expensive month). Booking January (the cheapest month) may end up saving you money.

  • Are there any Motel holiday rentals in Pittsfield?

    There are 2 holiday rentals in Pittsfield that fall under the Motel category, the most popular is Berkshire Inn.

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