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

Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is AU$260 per night from 18 May to 19 May
AU$260
18 May - 19 May
includes taxes & fees
Hotel On North: Pet-friendly hotel with free WiFi and free parking. Guests love the helpful staff!
My favorite place to stay in Pittsfield. Only half mile walk to hospital, so I have stayed there when I had to go for surgery. Friendly and helpful staff. Off street parking. Nice decor. Restaurant in hotel is tasty but an expensive steakhouse, but only a short walk away from other places to eat ...

Reviewed on 14 May 2026

Opens in a new windowHotel On North
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$166 per night from 24 May to 25 May
AU$166
24 May - 25 May
includes taxes & fees
Berkshire Mountain Lodge: Business-friendly lodge with free WiFi and free parking. Located next to a golf course.
Loved this place - and would probably come. again. My only issue is that check-out is at 10:00 am. I had friends staying there who were not checking out, so I was able to linger in their suite. I imagine that I could have eaten breakfast in the large sunny open lounge on the first floor - if this ...

Reviewed on 14 May 2026

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$177 per night from 17 May to 18 May
AU$177
17 May - 18 May
includes taxes & fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG: Pet-friendly hotel with free WiFi and free valet parking. Located near ski lifts.
Staff was nice. Room was clean. Parking lot was under construction. Had to park offsite. Wasn't a total inconvenience. One elevator was broken and the wait time was long each time we were trying to use.

Reviewed on 19 Apr 2026

Opens in a new windowHoliday Inn & Suites Pittsfield-Berkshires by IHG
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