Pittsfield Holidays

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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.

Pittsfield Holiday

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 NZ$180 per night from 30 Nov to 1 Dec
NZ$180
includes taxes & fees
30 Nov - 1 Dec
7.8/10 Good! (681 reviews)
Everyone was amazing!
"We stayed for two weeks and couldn’t have been happier with the service. Such nice people, and so understanding. Six stars if I could!"

Reviewed on 17 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 NZ$347 per night from 22 Nov to 23 Nov
NZ$347
includes taxes & fees
22 Nov - 23 Nov
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 NZ$171 per night from 2 Dec to 3 Dec
NZ$171
includes taxes & fees
2 Dec - 3 Dec
8.4/10 Very Good! (1,000 reviews)
"Room was clean, comfortable, and convenient. Dog Friendly! Will stay again!"

Reviewed on 11 Nov. 2024

Best Western Plus Berkshire Hills Inn & Suites
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?
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.