Pittsfield Holiday Packages

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Pittsfield Accommodation

With 21 accommodations in Pittsfield to select from, the tough part isn't finding a place to stay... it's finding the right place to stay. That’s where we come in.

Okay — it's not every day you get to go on holiday, so why don't you spend your break lounging around in a luxurious room at the Yankee Suites Extended Stay (20 W Housatonic St)? If you'd rather something comfy and easy on your bank balance, we've got a few awesome options as well. Start with the Berkshire Inn (150 W Housatonic St).

Car Hire in Pittsfield

Want to pick up some wheels downtown? The team at Enterprise (526 East St) will help you out with that.

Holidays to Pittsfield

Caught the travel bug and prescribed yourself a trip to Pittsfield? Excellent choice. But before you scratch that itch, it doesn't hurt to read up on a few things about where you're headed to.

Want to visualise where you'll be based? Pittsfield sits 180 kilometres west of the well-known city of Boston.

Roughly 45 000 people call this part of The Berkshires home. So, if you're wanting to meet some new mates, you shouldn't have too many dramas.

Top Pittsfield hotels

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 out of 5
1055 South Street, Pittsfield, MA
The price is AU$216 per night from 2 Oct to 3 Oct
AU$216
2 Oct - 3 Oct
includes taxes & fees
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG: Hotel with free breakfast and free WiFi. Located near theme parks.
An experience Of a lifetime!
"To whom it may concern, My wife & I were blessed beyond measures with Chris the recepcionista who was an amazing incredible human being who treated us like family. We needed some direction to southbridge Ma. He explain to us the best way to get there and back to the hotel. Also the other gentleman ..."

Reviewed on 16 Sept 2025

Opens in a new windowHoliday Inn Express & Suites Pittsfield - Berkshires by IHG
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is AU$193 per night from 28 Sept to 29 Sept
AU$193
28 Sept - 29 Sept
includes taxes & fees
Berkshire Mountain Lodge: Business-friendly lodge with free WiFi and free parking. Located near skiing.
"It was a great Stay where we had to it was a good area I would come back to this place again"

Reviewed on 21 Sept 2025

Opens in a new windowBerkshire Mountain Lodge
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
Fully refundable
The price is AU$186 per night from 29 Sept to 30 Sept
AU$186
29 Sept - 30 Sept
includes taxes & fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG: Pet-friendly hotel with free WiFi and free parking. Located near skiing.
"Valerie at the front desk and who checked me in was above and beyond in customer service. She checked to see if I had a IGH account—which I did but had forgotten, and reminded me about the points and promotions. This Holiday Inn is a well managed property. Thank you"

Reviewed on 18 Sept 2025

Opens in a new windowHoliday Inn & Suites Pittsfield-Berkshires by IHG
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.