Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Pittsfield Vacations

Pack those stellar shades. We have Pittsfield vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Pittsfield – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Pittsfield vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Pittsfield

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Pittsfield vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Pittsfield well.

Top Hotel Deals

See all 165 Hotels in Pittsfield
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St, Pittsfield
3.0 out of 5.0

Located in the heart of Pittsfield, this hotel is 1.7 mi (2.8 km) from Hancock Shaker Village and 2.9 mi (4.7 km) from Bousquet Ski Area. Colonial Theater and ...

$80

$80
Crowne Plaza Pittsfield-Berkshires

Crowne Plaza Pittsfield-Berkshires

1 West St, Pittsfield
4.0 out of 5.0

Located in the heart of Pittsfield, this hotel is within a 5-minute walk of Berkshire Museum, Colonial Theater, and Berkshire Athenaeum. Canoe Meadows Wildlife ...

$79

$79
Hotel On North

Hotel On North

297 North Street, Pittsfield
4.0 out of 5.0

Situated in Pittsfield, this hotel is within a 10-minute walk of Berkshire Museum, Berkshire Athenaeum, and Colonial Theater. Canoe Meadows Wildlife Sanctuary ...

$159

$159
Hilton Garden Inn Lenox/Pittsfield

Hilton Garden Inn Lenox/Pittsfield

1032 South Street, Pittsfield
3.5 out of 5.0

Situated in Pittsfield, this hotel is 1.2 mi (1.9 km) from Bousquet Ski Area and within 3 mi (5 km) of Arrowhead Museum and Kennedy Park. Colonial Theater and ...

$110

$110
Berkshire Mountain Lodge

Berkshire Mountain Lodge

8 Dan Fox Dr, Pittsfield
3.5 out of 5.0

Situated in Pittsfield, this lodge is close to Arrowhead Museum, Bousquet Ski Area, and Canoe Meadows Wildlife Sanctuary. Local attractions also include Kennedy ...

$178

$178
Berkshire Inn

Berkshire Inn

150 W Housatonic St, Pittsfield
2.5 out of 5.0

Located in the heart of Pittsfield, this motel is within a 15-minute walk of Colonial Theater and Berkshire Museum. Berkshire Athenaeum and Canoe Meadows Wildlife ...

$59

$59
Yankee Suites Extended Stay

Yankee Suites Extended Stay

20 W Housatonic St., Pittsfield
4.5 out of 5.0

Situated in Pittsfield, this guesthouse is within a 5-minute walk of Colonial Theater and Berkshire Museum. Berkshire Athenaeum and Canoe Meadows Wildlife Sanctuary ...

$85

$85
Econo Lodge

Econo Lodge

16 Cheshire Road, Pittsfield
2.0 out of 5.0

Situated in the suburbs, this motel is 1.6 mi (2.6 km) from Crane Museum of Papermaking and within 6 mi (10 km) of Berkshire Athenaeum and Colonial Theater. ...

$59

$59
White Horse Inn

White Horse Inn

378 South St, Pittsfield
3.5 out of 5.0

Situated in Pittsfield, this bed & breakfast is within 1 mi (2 km) of Colonial Theater, Berkshire Museum, and Berkshire Athenaeum. Canoe Meadows Wildlife Sanctuary ...

$135

$135
Heart of the Berkshires Motel

Heart of the Berkshires Motel

970 W Housatonic St, Pittsfield
2.5 out of 5.0

Situated in Pittsfield, this motel is within 3 mi (5 km) of Hancock Shaker Village, Colonial Theater, and Berkshire Museum. Berkshire Athenaeum is 2.8 mi (4.4 ...

$60

$60

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.