Pittsfield Vacations

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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 SAR 376 per night from Jun 8 to Jun 9
SAR 376
SAR 420 total
8 Jun - 9 Jun
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
"Very friendly staff. Greeted each time, coming in or going out. Breakfast was good, many varieties available, came with stay. Make your own waffles! Maybe I'm new to staying at Inns, motels, etc., as much as I have this year, but that was a pleasant surprise."

Reviewed on 4 June 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 SAR 409 per night from Jun 15 to Jun 16
SAR 409
SAR 457 total
15 Jun - 16 Jun
includes taxes & fees
7.8/10 Good! (789 reviews)
"Pleasant work staff"

Reviewed on 3 June 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (482 reviews)
"Everything I mean everything is so so clean They are wiping and dusting all the time"

Reviewed on 31 May 2025

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Berkshire Mountain Lodge
See all 1,341 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 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

Hardly anyone here! Great way to spend a week day, skiing and tubing!

Bousquet Ski Area

4/5(9 reviews)

Hit the slopes at Bousquet Ski Area during your trip to Pittsfield. Wander the lakeside in this quaint area.

Bousquet Ski Area
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

Hancock Shaker Village

4.5/5(53 reviews)

You can browse the exhibits at Hancock Shaker Village, a museum with a storied past, during your trip to Pittsfield. Wander the lakeside in this quaint area.

Hancock Shaker Village