Pittsfield Vacations from $339

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Your Pittsfield Vacation

When you book a Pittsfield vacation package, you can kick back and enjoy your escape to the fullest. Delve into the highlights of this exciting city knowing that all your travel arrangements have been looked after before you go. A trip to Pittsfield is a wonderful opportunity to sightsee. Be sure to stop by big-name attractions such as Bousquet Ski Area, Colonial Theater and Hancock Shaker Village. Expedia will help you escape the everyday. Tailor your vacation to Pittsfield to suit your style of travel, whatever that may look like.

The Latest Pittsfield vacation packages

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Lake George/Warrensburg Area
La Quinta Inn & Suites by Wyndham Lake George
Sundowner on Lake George
Lodges At Cresthaven
Hotel Brookmere & Arbor Spa
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Discover the most popular places to visit in Pittsfield

Pittsfield Hotel Deals

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $141 total per night from Jul 27 to Jul 28
$141 total
Jul 27 - Jul 28
Total includes taxes and fees
8.4/10 Very Good! (1,012 reviews)
"Great"

Reviewed on Jul 13, 2025

Best Western Plus Berkshire Hills Inn & Suites
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
$129 nightly
The price is $144 total per night from Jul 27 to Jul 28
$144 total
Jul 27 - Jul 28
Total includes taxes and fees
7.8/10 Good! (822 reviews)
Very solid spot
"Great spot for exploring the area. Walking distance to downtown, and easy drive to nature, which is why I was in town w/ friends. Only complaint is that the hot water ran out really fast in the showers the days we were there"

Reviewed on Jul 16, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$70 nightly
The price is $79 total per night from Aug 5 to Aug 6
$79 total
Aug 5 - Aug 6
Total includes taxes and fees
5.2/10 (741 reviews)
"Rooms were much nicer than expected. Despite the somewhat dated exterior and overall first impression from the outside, the rooms were solidly good, clean, and comfortable. Good value for the price."

Reviewed on Jul 1, 2025

FairBridge Inn Express
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.

Find the Best Pittsfield Vacation Packages

Pittsfield Essential Information

Language
English
Currency
U.S dollars
Population
43,300
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Bousquet Ski Area, Colonial Theater and Barrington Stage Company

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Frequently asked questions

How much does a Pittsfield vacation package cost?
You can grab a vacation package to this popular destination from $339 on Expedia. But how much your vacation to Pittsfield costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Pittsfield?
October, November and December are great times to look for cheap Pittsfield vacation packages. Opting to travel in less busy periods means you can generally find reduced prices on flights and accommodations.
How many days is enough for Pittsfield?
The ideal duration of your Pittsfield vacation depends on what you'd like to do. Typically, a handful of days to a week will give you plenty of time to check out all the leading attractions and discover some hidden treasures along the way.
Is it worth booking a vacation package to Pittsfield?
Pittsfield offers everything you need for an unforgettable getaway. Begin your Pittsfield vacation on a high note by checking out major attractions like Bousquet Ski Area.
How to find the best Pittsfield package deals?
Landing a cheap Pittsfield package deal is a breeze with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget range, apply a few filters and see what's available. You can tailor your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Pittsfield package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Pittsfield vacation as a package?
You can enjoy significant savings on your Pittsfield retreat by booking a personalized vacation package. Click on the "Package" heading, then enter your destination and travel dates to see the best airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Pittsfield?
If you have your Pittsfield travel dates finalized, book as soon as you can to score some unbeatable deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Pittsfield vacation packages?
Your Pittsfield trip should be a relaxing escape from your daily routine, not a source of money worries. So to give you extra flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.