Pittsfield Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence
    • payments icon
    Better together
    Save up to AU$703 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

Your Pittsfield Holiday

When you book a Pittsfield holiday package, you can kick back and enjoy your getaway to the fullest. Uncover the best parts of this unique city knowing that all your travel arrangements have been looked after before you go. Make your trip to Pittsfield even more fulfilling by including some sightseeing. Bousquet Ski Area, Hancock Shaker Village and Pittsfield State Forest are among the big attractions worth exploring. That dream Pittsfield holiday is a couple of clicks away. Explore hotels, flights and more on Expedia for a getaway that's tailored to suit your style.

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Pittsfield Holiday

Pittsfield Essential Information

Language
English
Currency
U.S dollars
Population
43,300
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Jiminy Peak Mountain Resort, Norman Rockwell Museum and Bousquet Ski Area

Our pick of the best Pittsfield Hotel Deals

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 AU$171 per night from 29 Nov to 30 Nov
AU$171
includes taxes & fees
29 Nov - 30 Nov
7.8/10 Good! (684 reviews)
"The restaurant is as great!"

Reviewed on 25 Nov. 2024

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundable
The price is AU$315 per night from 4 Dec to 5 Dec
AU$315
includes taxes & fees
4 Dec - 5 Dec
8.8/10 Excellent! (411 reviews)
"Loved our room. Very clean"

Reviewed on 19 Nov. 2024

Berkshire Mountain Lodge
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 AU$156 per night from 3 Dec to 4 Dec
AU$156
includes taxes & fees
3 Dec - 4 Dec
8.4/10 Very Good! (1,002 reviews)
"Room was clean, comfortable, and convenient. Dog Friendly! Will stay again!"

Reviewed on 11 Nov. 2024

Best Western Plus Berkshire Hills Inn & Suites
See all 1,245 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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a Pittsfield holiday package cost?
Choose from any combination of flights, hotels and car rentals, and you can be holidaying in Pittsfield from just . And the more you bundle, the more money you save. The holiday of your dreams has never been so affordable.
How do I get a cheap travel package to Pittsfield?
You’ll save a ton of money if you bundle your flights, hotels and car rentals into a Pittsfield holiday package. Sometimes cheap means fewer options. But not with Expedia. We offer over 550 partner airlines and 1 000 000 properties worldwide, so you’ll always have plenty of variety to choose from. Eager to save even more? Add some interesting activities to your package deal to unlock even more discounts! After all, travel is about more than simply getting to your destination.
Where should I stay in Pittsfield?
With so much to do in Pittsfield, we recommend you book a room in a hotel close to its attractions. Bousquet Ski Area, Hancock Shaker Village and Barrington Stage Company are some good ones to add to your must-see list.
What are the top hotels in Pittsfield?
Berkshire Mountain Lodge and 2/bedroom Historic District - Long Term Homes Welcome are two of the most popular properties in Pittsfield. Why not look up the facilities and rates at each and then make up your mind?
How far in advance should I book my Pittsfield holiday?
Browse Expedia to compare international flights ASAP. In many cases, you can purchase a seat up to a year in advance. If you don’t see your preferred carrier, or you’ve left things to the last minute, don’t stress. The lowest prices to Pittsfield occasionally appear within weeks of the date of departure.
What does an Expedia Pittsfield travel package include?
Choose from a combination of hotels, rental cars and flights. Once you’ve made your booking, you can also add on activities and tours. Want to pick your airfare class? That’s also possible. The choice is all yours when it comes to planning your ideal Pittsfield escape.
What should I know before booking a Pittsfield travel package?
Whether it’s relaxation or adventure you’re craving, a Pittsfield holiday package lets you organise your escape your way. Plus, you’ll score great discounts when you combine your accommodation with your flights and rental car. The more you bundle, the more you’ll save!
Can I choose my airline with a Pittsfield Expedia holiday package?
Yes — and it’s easy too. Expedia has access to more than 550 partner airlines throughout the world. Our packages give you the freedom to take your pick of available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Pittsfield holiday package?
It’s impossible to predict what the future holds, so it’s good to know that you can change or cancel your Pittsfield holiday package. If your booking was made in the last 24 hours, you may be eligible for a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal to learn more.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.