Pittsfield Vacation Packages

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Your Pittsfield Vacation

When you book a Pittsfield vacation package, you can kick back and enjoy your escape to the fullest. Delve into the highlights of this exciting city knowing that all your travel arrangements have been looked after before you go. A trip to Pittsfield is a wonderful opportunity to sightsee. Be sure to stop by big-name attractions such as Bousquet Ski Area, Colonial Theater and Hancock Shaker Village. Expedia will help you escape the everyday. Tailor your vacation to Pittsfield to suit your style of travel, whatever that may look like.

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 CA $143 per night from May 27 to May 28
CA $143
CA $159 total
includes taxes & fees
May 27 - May 28
7.8/10 Good! (580 reviews)
"loved how close to downtown the property is, we walked whwre we could. parking garage is closed for renovations but the staff was great and provided free valet and parked our car close or in front of the doors most days to help with us having a small child and my husband using a cane. loved the bar ..."

Reviewed on May 18, 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 CA $149 per night from May 29 to May 30
CA $149
CA $167 total
includes taxes & fees
May 29 - May 30
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 May 14, 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 CA $202 per night from May 28 to May 29
CA $202
CA $253 total
includes taxes & fees
May 28 - May 29
8.8/10 Excellent! (311 reviews)
"A good stay. Clean and quite. Nice pool and fun for the Kidspiration"

Reviewed on May 5, 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.

Explore other types of vacation packages

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Frequently asked questions

How much does a Pittsfield vacation package cost?
Choose from any combination of flights, hotels and car rentals, and you can be vacationing in Pittsfield from just . And the more you bundle, the more money you save. The vacation 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 vacation 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 Rentals 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 vacation?
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 vacation package lets you organize your escape your way. Plus, you’ll score great discounts when you combine your accommodations with your flights and rental car. The more you bundle, the more you’ll save!
Can I choose my airline with a Pittsfield Expedia vacation 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 vacation package?
It’s impossible to predict what the future holds, so it’s good to know that you can change or cancel your Pittsfield vacation 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.

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 exploring the galleries in Berkshire Museum during your trip to Pittsfield. Wander the lakeside in this family-friendly area.

Berkshire Museum
Image for Hancock Shaker Village

Hancock Shaker Village

4.5/5(3 reviews)

You can browse the exhibits at Hancock Shaker Village, a museum with a storied past, during your trip to Pittsfield. Wander the lakeside in this quaint area.

Hancock Shaker Village

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