Pittsfield Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Pittsfield

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 2.616.807 ₫ per night from 30 Jun to 1 Jul
2.616.807 ₫
2.922.973 ₫ total
30 Jun - 1 Jul
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
"I loved everything about this hotel! It was PERFECT! This is my favorite hotel!"

Reviewed on 23 Jun 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 3.209.685 ₫ per night from 24 Jul to 25 Jul
3.209.685 ₫
3.585.218 ₫ total
24 Jul - 25 Jul
includes taxes & fees
7.8/10 Good! (797 reviews)
"All was great, except parking was quiet of walk"

Reviewed on 13 Jun 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 1.855.354 ₫ per night from 13 Jul to 14 Jul
1.855.354 ₫
2.072.430 ₫ total
13 Jul - 14 Jul
includes taxes & fees
5.2/10 (728 reviews)
"The stay was okay until the front desk clerk tried coming into our room before checkout time. My wife and I were not even decently dressed. It was 10:15 am. Checkout is 11 am. Not satisfied."

Reviewed on 22 Jun 2025

FairBridge Inn Express
See all 1,344 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 holiday package cost?
You can grab a holiday package to this popular destination on Expedia. But how much your holiday 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 holiday packages. Travelling 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 holiday. 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 holiday package to Pittsfield?
Pittsfield is a good holiday 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 holiday 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 travelling on a weekday, when prices are often lower.
Is it cheaper to book a Pittsfield holiday as a package?
You can enjoy significant savings on your Pittsfield retreat by booking a personalised holiday package. Click on the "Package" heading, then enter your destination and travel dates to see the best airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday 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 holiday. 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 holiday package that brings all your bookings together.

Popular places to visit

Bousquet Ski Area

Bousquet Ski Area

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

Bousquet Ski Area
Berkshire Museum

Berkshire Museum

You can spend an afternoon studying the exhibits at Berkshire Museum in Pittsfield. Wander the lakeside in this family-friendly area.

Berkshire Museum

Hancock Shaker Village

5/5(2 reviews)

You can browse the exhibits at Hancock Shaker Village, a museum with a story of its own, during your travels to Pittsfield. Wander the lakeside in this quaint area.

Hancock Shaker Village