Pittsfield Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to ₩234,741 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Find the Best Pittsfield Vacation Packages

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
The price is ₩149,010 per night from Jul 1 to Jul 2
₩149,010
₩166,445 total
Jul 1 - Jul 2
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
"I loved everything about this hotel! It was PERFECT! This is my favorite hotel!"

Reviewed on Jun 23, 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
The price is ₩167,412 per night from Jul 24 to Jul 25
₩167,412
₩186,999 total
Jul 24 - Jul 25
includes taxes & fees
7.8/10 Good! (801 reviews)
"Quick check in. Room was clean, beds were comfortable. Employees were pleasant. Free valet was a big plus +++"

Reviewed on Jun 28, 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
The price is ₩96,772 per night from Jul 13 to Jul 14
₩96,772
₩108,096 total
Jul 13 - Jul 14
includes taxes & fees
5.4/10 (732 reviews)
"Shampoo and toilet paper should have been In the room."

Reviewed on Jun 29, 2025

FairBridge Inn Express
See all 1,345 properties in Pittsfield
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.

Frequently asked questions

How much does a Pittsfield vacation package cost?
You can grab a vacation package to this popular destination 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?
January, March and April are the best times to search for cheap Pittsfield vacation packages. Traveling in less busy months means you can generally find lower prices on flights and hotels.
How many days is enough for Pittsfield?
Usually, a handful of days is enough to check out the major sights during your Pittsfield vacation. But if you prefer to have more time to kick back or take day trips, think about extending your itinerary.
Is it worth booking a vacation package to Pittsfield?
Pittsfield is a good vacation destination with attractions like Bousquet Ski Area among the many things to keep you busy. Whether you're heading away with the family or planning a trip with friends, a Pittsfield vacation promises fun for everyone.
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.
How to plan a trip to Pittsfield?

  1. Choose the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Pittsfield.
  2. Work out your budget: Make sure you have enough money to pay for everything from transportation and meals to flights and activities. Your hotel will probably be the biggest expense during your trip to Pittsfield.
  3. Decide how long to go for: Now that you know more about Pittsfield, you can work out the ideal length of your vacation. Create a draft plan and allocate enough time to cover everything you want to do.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to choose a Pittsfield vacation package that brings all your bookings together.

Discover the most popular places to visit in Pittsfield

View of peak foliage in the Berkshires.

Berkshire Museum

You can spend an afternoon exploring the galleries in Berkshire Museum during your trip to Pittsfield. Wander the lakeside in this family-friendly area.

Berkshire Museum
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.