Holiday package deals in Pittsfield

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Tips for booking hotels in Pittsfield

Gain useful insights to help choose a hotel in Pittsfield. Data was last updated on Tue Mar 24 2026.
Cheapest month:February
Most expensive month:July
Average price in Pittsfield:£128/night
Cheapest price found:£55/night
Cheapest day:Tuesday
Most expensive day:Friday
£96 - £236
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.
£101 - £158
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.

Popular Pittsfield vacation deals

Users browsing Cheapflights choose these holiday deals more than any other. Data was last updated on Tue Mar 24 2026.
The Red Lion Inn
The Red Lion Inn

The Red Lion Inn

30 Main Street, Stockbridge, MA, United States
0.0 mi from city centre
Free Wi-Fi
Parking
£1,239
Avg. per night
View Deal
Holiday Inn & Suites Pittsfield-Berkshires By IHG
Holiday Inn & Suites Pittsfield-Berkshires By IHG

Holiday Inn & Suites Pittsfield-Berkshires By IHG

1 West Street, Pittsfield, MA, United States
0.0 mi from city centre
Pool
Free Wi-Fi
£918
Avg. per night
View Deal
Vacation Village in the Berkshires
Vacation Village in the Berkshires

Vacation Village in the Berkshires

Hancock, MA, United States
0.0 mi from city centre
Air conditioning
Pool
£808
Avg. per night
View Deal
The Whitlock by The Lenox Collection
The Whitlock by The Lenox Collection

The Whitlock by The Lenox Collection

16 Church Street, Lenox, MA, United States
0.0 mi from city centre
Free Wi-Fi
Parking
£1,396
Avg. per night
View Deal
The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

203 Main Street, Lenox, MA, United States
0.0 mi from city centre
Free Wi-Fi
Parking
£1,355
Avg. per night
View Deal
Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

445 Pittsfield Road, Lenox, MA, United States
0.0 mi from city centre
Pool
Free Wi-Fi
Parking
£1,349
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
0.0 mi from city centre
Free Wi-Fi
Parking
£839
Avg. per night
View Deal
See all

Where to stay in Pittsfield

Utilise the map to find the perfect place to stay for your trip to Pittsfield. There are 17 hotels to choose from in Pittsfield.

FAQ about Pittsfield holiday packages

Find answers to frequently asked questions Cheapflights users have about Pittsfield holiday deals.

  • How much are vacation packages to Pittsfield?

    Pittsfield holidays can be booked for as little as £808.

  • What is the cheapest time of year to travel to Pittsfield?

    If you're looking for the cheapest month of the year to book a holiday package to Pittsfield, January is ideal.

  • Can I save money on travel by booking a holiday package with Cheapflights?

    Make sure to check back regularly as prices are subject to change.

  • What other destinations does Pittsfield have flight+hotel deals to?

    In addition to Pittsfield, Cheapflights also offers holiday packages to Massachusetts

See more FAQs

Other popular holiday deals in Massachusetts

Consider booking a Flight+Hotel in one of these other areas of Massachusetts.
Massachusetts holidays
Boston holidays
Salem holidays
Bedford holidays
Burlington holidays
Waltham holidays
Cambridge holidays
Peabody holidays
Quincy holidays
Springfield holidays
Worcester holidays