Pittsfield Holidays

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Your Pittsfield Holiday

Entertainment, food, art and more … There's so much to immerse yourself in with a Pittsfield holiday package. And with the ability to easily customize your city getaway, you know it'll be one you won't forget. Fill up your itinerary with tours of Bousquet Ski Area, Hancock Shaker Village and Barrington Stage Company, some of the top attractions you shouldn't miss during a trip to Pittsfield. Your perfect Pittsfield holiday is a few clicks away. Search accommodation, flights and more on Expedia for a getaway that's tailored just for you.

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
Stay at this business-friendly hotel in Pittsfield. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
7.8/10 Good! (579 reviews)
"You walk in and you’re greeted with a smile, you’re treated respectfully and everyone is so very helpful! Second time I’ve stayed here in a year and it is the only place I’m going to book when I’m in the area."

Reviewed on 10 May 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
Stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
8.4/10 Very Good! (943 reviews)
"The hotel was farther off of the freeway than I thought it would be. But it was a nice quiet room with a good breakfast. The workout room had a decent treadmill. The stepper needed a battery and the Peloton needed help from the employee to connect to the internet so we didn't ask. The staff was super ..."

Reviewed on 14 May 2024

Best Western Plus Berkshire Hills Inn & Suites
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Stay at this 3-star golf lodge in Pittsfield. Enjoy free Wi-Fi, free parking and a fitness centre. Our guests praise the clean rooms in their reviews. Popular ...
8.8/10 Excellent! (311 reviews)
"A good stay. Clean and quite. Nice pool and fun for the Kidspiration"

Reviewed on 5 May 2024

Berkshire Mountain Lodge
See all 1,228 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

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Pittsfield travel package cost?
Get your credit card ready, because a trip to Pittsfield starts from only . When you combine your hotels, flights and car rentals into a travel package, you’ll pick up the biggest deals.
If I'm not able to travel, can I cancel my Pittsfield travel package?
Whether it’s your hotel or flight, you can cancel or amend it. Booked your Pittsfield travel package in the last 24 hours? You may be able to make changes for free. If it’s been longer than that, you may be charged a fee by your hotel, airline or car rental company. For further information, visit our Customer Service Portal. We’re here to help you every step of the way.
How do I get a cheap travel package to Pittsfield?
Combine your flights and hotels, throw in extras such as activities, and save with a Pittsfield travel package. You won’t just score big discounts on your trip — you’ll have plenty of choice at your fingertips too. When you book with Expedia, you can select from more than 550 air carriers and 1,000,000 properties throughout the world. Your next epic adventure begins right here, right now!
Does Expedia offer Book Now, Pay Later Pittsfield holidays?
Expedia has joined forces with online lender Klarna to make booking your next trip easier on your budget. Paying by instalment means you can spread the costs of your dream holiday, leaving you with more money to play with while you’re away. Klarna has several payment plans to choose from, so you’re sure to find one that fits your budget. Check out these flexible payment options:

  • Pay monthly holidays: If paying small amounts each month is something that would work for you, Klarna can help. Paying in easy monthly instalments will make your getaway dreams come true.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay for your trip in multiple transactions.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the total upfront) makes it easier to click that “book now” button, opt for a low deposit holiday payment plan with Klarna.

Where should I stay in Pittsfield?
With loads to discover in Pittsfield, it’d be handy for you to lock in a hotel near its attractions. Bousquet Ski Area, Hancock Shaker Village and Pittsfield State Forest are some good ones to put on your to-do list.
What are the top hotels in Pittsfield?
Make a reservation at Holiday Village In The Berkshires. It’s one of this neighbourhood’s most popular properties. Another top-rated option in Pittsfield is The Black Swan Lee - Lenox, Ascend Hotel Collection.
How far in advance should I book my Pittsfield holiday?
Travellers are normally able to browse international flights on Expedia within 12 months of the departure date. Booking at the last minute? With a little bit of luck, it’s still possible to score an affordable ticket only weeks before your flight.
What does an Expedia Pittsfield travel package include?
With Expedia, you can choose any combination of car rentals, flights and hotels to create your perfect Pittsfield travel package. Once you’ve made your booking, you can add on the fun stuff like sightseeing tours and activities. Don’t forget, the more you bundle, the more dollars you’ll save!
What should I know before booking a Pittsfield travel package?
You’ll score amazing savings when you bundle your hotels, flights and rental cars into a travel package. Not only that, booking everything in one spot just makes things easier. So why waste your money or time? Whether you’re putting together a luxury city stay with your love or an affordable family break, take a look at our package deals today.
Can I choose my airline with a Pittsfield Expedia travel package?
Yes, of course. We have more than 550 airline partners around the world, so select the carrier that best suits your budget and travelling style.

Discover the most popular places to visit in Pittsfield

Image for Bousquet Ski Area

Bousquet Ski Area

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

Bousquet Ski Area
Image for 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
Image for Hancock Shaker Village

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

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.