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$193 per night from 16 Mar to 17 Mar
AU$193
includes taxes & fees
16 Mar - 17 Mar
Hotel On North: Pet-friendly hotel with free WiFi and free parking. Guests love the helpful staff!
Great but noisey on Saturday nights
"This is my second time staying and I love the attention to detail. However I happened to be there on a Saturday in room 202 and I could hear the dj music in my room till 1 am. This seems like it will be a regular Saturday night thing in the dining room. I would inquire about the quietness of your ..."

Reviewed on 12 Mar. 2025

Hotel On North
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundable
The price is AU$210 per night from 23 Mar to 24 Mar
AU$210
includes taxes & fees
23 Mar - 24 Mar
Berkshire Mountain Lodge: Business-friendly lodge with free WiFi and free parking. Located next to a golf course.
Second stay
"Great place, super friendly staff, pool is nice n big and warm- not an overly chlorine smell too lol - price is good especially for a kitchen/living room set up and a bedroom. Second time staying - we will be back 😀"

Reviewed on 10 Mar. 2025

Berkshire 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$184 per night from 21 Mar to 22 Mar
AU$184
includes taxes & fees
21 Mar - 22 Mar
Holiday Inn & Suites Pittsfield-Berkshires by IHG: Pet-friendly hotel with free WiFi and free parking. Located near ski runs.
Very good experience
"Arrived late and restaurant staff were very helpful preparing me a late night take out meal. Breakfast very good. Allowed me to check out late as I was waiting for a ride."

Reviewed on 12 Mar. 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
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