Pittsfield Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Pittsfield

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
3 out of 5
One West Street, Pittsfield, MA
Fully refundable
The price is 2.520.045 ₫ per night from 5 Jan to 6 Jan
2.520.045 ₫
2.814.814 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2025
7.8/10 Good! (701 reviews)
"Staff was very accommodating. The pool area was quite nice and it was deep"

Reviewed on 16 Dec 2024

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
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 2.400.152 ₫ per night from 1 Jan to 2 Jan
2.400.152 ₫
2.680.969 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2025
8.4/10 Very Good! (1,000 reviews)
"The bed was comfortable and room was nice."

Reviewed on 10 Dec 2024

Best Western Plus Berkshire Hills Inn & Suites
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundable
The price is 4.200.075 ₫ per night from 1 Jan to 2 Jan
4.200.075 ₫
5.200.711 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2025
8.8/10 Excellent! (416 reviews)
"It was very conveniently located to the activities we were doing on our mini-vacation. There were a couple of issues that developed during our stay, but the staff did an excellent job of dealing with the issues."

Reviewed on 5 Dec 2024

Berkshire Mountain Lodge
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.
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.

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