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.

Top Pittsfield Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Manchester View

The Manchester View

2.5 out of 5
per person
Dec. 13 - Dec. 17
found 18 hours ago
Roundtrip flight included
Detroit (DTW) to Albany (ALB)
9.4/10 Exceptional! (616 reviews)
Beautiful Views.. nice quiet place to stay

Reviewed on Sep. 18, 2024

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
per person
Dec. 13 - Dec. 17
found 18 hours ago
Roundtrip flight included
Detroit (DTW) to Albany (ALB)
7.4/10 Good! (403 reviews)
We loved the property and the staff was excellent.

Reviewed on Sep. 22, 2024

South Shire

South Shire

4 out of 5
per person
Dec. 13 - Dec. 17
found 18 hours ago
Roundtrip flight included
Detroit (DTW) to Albany (ALB)
9.4/10 Exceptional! (68 reviews)
Lovely Victorian building. The owner was wonderful! We’ll be back!

Reviewed on Aug. 16, 2024

Pinnacle Lodge

Pinnacle Lodge

2 out of 5
per person
Dec. 13 - Dec. 17
found 18 hours ago
Roundtrip flight included
Detroit (DTW) to Albany (ALB)
10/10 Exceptional! (1 review)

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Pittsfield Hotel Deals

FairBridge Inn Express
FairBridge Inn Express
2.5 out of 5
16 Cheshire Road, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is CA $107 per night from Sep. 24 to Sep. 25
CA $107
CA $120 total
includes taxes & fees
Sep 24 - Sep 25
5.2/10 (649 reviews)
"great for the price"

Reviewed on Sep. 22, 2024

FairBridge Inn Express
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundable
The price is CA $226 per night from Sep. 24 to Sep. 25
CA $226
CA $280 total
includes taxes & fees
Sep 24 - Sep 25
8.8/10 Excellent! (372 reviews)
"Loved the suite and amenities for the price"

Reviewed on Sep. 21, 2024

Berkshire Mountain Lodge
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 $161 per night from Oct. 22 to Oct. 23
CA $161
CA $180 total
includes taxes & fees
Oct 22 - Oct 23
7.8/10 Good! (648 reviews)
"We had a great stay. Out in room refrigerator was t working but after calling the front desk, it was quickly replaced. Shower head placement was a bit unusual but after the first night of limited hot water, it was back to hot the rest of our stay. Towels were replaced frequently. Beds were comfortable. ..."

Reviewed on Sep. 21, 2024

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
See all 1,241 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 Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

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 CA $972. 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.