Pittsfield Trips (flight + hotel)

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Top hotels in Pittsfield

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! (542 reviews)
"Overall great. Located to many of the attractions in area. Grocery store across the street. Only downfall was the room was noisy in the night from being on ground floor. Other than that can not beat the quality for the price!"

Reviewed on Aug 4, 2025

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Berkshire Mountain Lodge
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 P4,089 per night from Aug 21 to Aug 22
P4,089
P4,567 total
Aug 21 - Aug 22
includes taxes & fees
5.2/10 (761 reviews)
"This family is professional and kind. I left a $100 tip because I watched attend to her guests and her two Autistic sons as well as her elderly parent. Amazing"

Reviewed on Aug 2, 2025

FairBridge Inn Express
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 P6,613 per night from Sep 1 to Sep 2
P6,613
P7,387 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (849 reviews)
"Consistently a clean room with welcoming staff."

Reviewed on Aug 5, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
See all 1,358 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.

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