Book Exclusive Pittsfield Vacation Packages

Choose one or more items to build your trip:

Pittsfield flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was CA $910, price is now CA $780 per person
CA $780
per person
Oct 19 - Oct 23
found 4 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Albany (ALB)
Book a stay at this family-friendly aparthotel in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.
Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
Price was CA $1,417, price is now CA $1,003 per person
CA $1,003
per person
Nov 2 - Nov 6
found 4 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Albany (ALB)
Book a stay at this beach lodge in Lake George. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Lake George Steamboat Company and Fort William Henry Museum are located nearby.
South Shire

South Shire

4 out of 5
Price was CA $1,294, price is now CA $943 per person
CA $943
per person
Nov 2 - Nov 6
found 4 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Albany (ALB)
Stay at this B&B in Bennington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Bennington Arts Guild Gallery and Fiddlehead at Four Corners are located nearby.
The Whitlock

The Whitlock

2 out of 5
Price was CA $1,218, price is now CA $982 per person
CA $982
per person
Oct 19 - Oct 23
found 4 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Albany (ALB)
Stay at this hotel in Lenox. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and The Bookstore are located nearby.
Hill Farm Inn

Hill Farm Inn

4 out of 5
Price was CA $1,364, price is now CA $1,123 per person
CA $1,123
per person
Nov 2 - Nov 6
found 4 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Albany (ALB)
Stay at this B&B in Arlington. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mount Equinox and Norman Rockwell Exhibition are located nearby.

Top Pittsfield hotels deals

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free cancellation
Reserve now, pay when you stay
The price is CA $131 per night
CA $131
CA $178 total
Aug 31 - Sep 1
includes taxes & fees
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road Pittsfield MA
The price is CA $80 per night
CA $80
CA $90 total
Sep 27 - Sep 28
includes taxes & fees
Book a stay at this business-friendly motel in Pittsfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Crane Museum of Papermaking and Crane Museum of Papermaking are located nearby.
Parking included
Free WiFi
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

2.5 out of 5
1055 South Street Pittsfield MA
Free cancellation
The price is CA $165 per night
CA $165
CA $184 total
Sep 24 - Sep 25
includes taxes & fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
Pool
Hot tub
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Free cancellation
The price is CA $165 per night
CA $165
CA $184 total
Sep 24 - Sep 25
includes taxes & fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Berkshire Museum and Colonial Theater are located nearby.
Pool
Pet-friendly
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
Free cancellation
Reserve now, pay when you stay
The price is CA $159 per night
CA $159
CA $178 total
Sep 20 - Sep 21
includes taxes & fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Tracy Brook Wildlife Sanctuary are located nearby.
Breakfast included
Pet-friendly
Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
Free cancellation
Reserve now, pay when you stay
The price is CA $248 per night
CA $248
CA $277 total
Sep 7 - Sep 8
includes taxes & fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Barrington Stage Company and Lichtenstein Center for the Arts are located nearby.
Pet-friendly
Parking included
Don't see what you're looking for?
See all available properties in Pittsfield
View all properties
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.

Stay near popular Pittsfield attractions

A historic stone building with a yellow roof, surrounded by a white fence and lush green grass.

Hancock Shaker Village

9.2/10 (101 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.
See properties

Pittsfield Vacations

Traveling is about feeling inspired, making new discoveries and collecting meaningful memories. And all of that begins with learning a thing or two about your destination! Are you ready to discover a few details about Pittsfield?

To help you get your bearings, Pittsfield is 110 miles (177 kilometers) to the west of the notable city of Boston.

There are around about 45,000 friendly locals that reside in this corner of The Berkshires.

Places to visit in Pittsfield

History has infinite lessons. Drink in the knowledge and better acquaint yourself with the past at Arrowhead Museum. Like some more options? There's nothing as exciting as gazing at a blanket of powder snow and knowing you've got an entire day ahead to tear up the slopes. Dig out your goggles and clip on your skis — Bousquet Ski Area is waiting for you! But there's more. The protection of special habitats, plant and animal species is increasingly important. Appreciate the peacefulness of nature at Canoe Meadows Wildlife Sanctuary and see what types of animals have made it their home.

Where do you fly into for Pittsfield?

Coming in to land at Bradley International Airport (BDL)? Once you step off the aircraft, the middle of Pittsfield is approximately 45 miles (72 kilometers) northwest from here. Call a cab and enjoy the journey — your adventure is just beginning!

Frequently asked questions

How much are vacation packages to Pittsfield?
With a Travelocity vacation package, you can live it up in Pittsfield for as low as CA $780. Flights, hotels and experiences — we've got you. You can save some cash just for combining your bookings. With all of that taken care of before you even set off, you won't have to worry about a thing.
How long should my Pittsfield vacation be?
Your Pittsfield break can be as short or as long as you'd like it to be, but the majority of travelers stay roughly 2 nights. Hoping to veer off the beaten path and discover some hidden gems? Book a couple more nights and see another side of this place.
Where can I get the best vacation package deals for Pittsfield?
It's hard to beat Travelocity when it comes to putting together your Pittsfield package deal. There are at least 400 airlines and 1,000,000 properties worldwide to select from. Book your trip now and get ready to tick another exciting place off your to-do list.
Why should I book my Pittsfield vacation bundle with Travelocity?
From our 24/7 support to our range of exhilarating destinations, we are dedicated to fulfilling your vacation dreams. All you'll have to do is click and book — our Price Match Guarantee will ensure you get the best deal.
Can I save money on my Pittsfield car rental if I combine it with hotels and flights?
With a Pittsfield vacation package, you can bundle your hotel, car and flight bookings and save a ton. If you want to uncover the best of this fantastic area, why not start with Times Square? This renowned sight is 193 kilometers from Pittsfield. With your own rental car, you'll be there in no time.
Which airport is best for Pittsfield?
Bradley Intl. Airport (BDL) is 72 kilometers from the city center and is the starting point for many exciting adventures. Alternatively, Albany Intl. Airport (ALB) is 56 kilometers away from central Pittsfield and Hartford, CT (HFD-Hartford - Brainard) is 97 kilometers away from central Pittsfield.
What is there to do in Pittsfield?
Pittsfield has plenty of places to explore, such as Bousquet Ski Area and Barrington Stage Company. These two impressive attractions top most travelers' itineraries.
Where should I stay when visiting Pittsfield?
Many travelers opt to spend their nights at the Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel. It's the perfect base for your Pittsfield vacation.

Photos of local treasures

Browse Pittsfield vacation photos for more inspiration

A historic building with classical architecture, a traffic light, and a yellow taxi.
A stone building with a red door and a tree with pink flowers in front.
A brick building with a clock and an American flag.
A stone church with arched windows and a central tower, surrounded by trees.
A street lined with autumn trees, a street lamp, and parked cars.