Book Exclusive Pittsfield Vacation Packages

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Pittsfield flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
The White House Inn

The White House Inn

3.5 out of 5
Price was CA $1,156, price is now CA $1,065 per person
CA $1,065
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
Stay at this hotel in Wilmington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions South Main Street and Pettee Memorial Library are located nearby.
Marriott Albany

Marriott Albany

3.5 out of 5
Price was CA $1,376, price is now CA $1,235 per person
CA $1,235
per person
Dec 22 - Dec 27
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
Book a stay at this business-friendly hotel in Albany. Enjoy an outdoor pool, a free airport shuttle, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Colonie Center Mall and Palace Theater are located nearby.
Saratoga Casino Hotel

Saratoga Casino Hotel

4 out of 5
Price was CA $1,386, price is now CA $1,247 per person
CA $1,247
per person
Dec 22 - Dec 27
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
Stay at this hotel in Saratoga Springs. Enjoy free WiFi, free parking, and a casino. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Saratoga Racetrack and Saratoga Performing Arts Center are located nearby.
The Landing Hotel at Rivers Casino Schenectady

The Landing Hotel at Rivers Casino Schenectady

4 out of 5
Nothside
Price was CA $1,662, price is now CA $1,510 per person
CA $1,510
per person
Dec 22 - Dec 27
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
Book a stay at this business-friendly hotel in Schenectady. Enjoy free WiFi, free parking, and 5 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Rivers Casino & Resort and Schenectady Light Opera Performing Arts Center are located nearby.
Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was CA $1,286, price is now CA $1,183 per person
CA $1,183
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this golf hotel in Wilmington. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mount Snow and North Branch Deerfield River 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 $116 per night
CA $116
per night
Nov 8 - Nov 9
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.
Pool
Hot tub
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 $162 per night
CA $162
per night
Nov 29 - Nov 30
Book a stay at this family-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
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 $144 per night
CA $144
per night
Nov 30 - Dec 1
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
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road Pittsfield MA
The price is CA $90 per night
CA $90
per night
Nov 1 - Nov 2
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 Barrington Stage Company are located nearby.
Parking included
Free WiFi
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 $131 per night
CA $131
per night
Nov 2 - Nov 3
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
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4 out of 5
20 W Housatonic St. Pittsfield MA
The price is CA $138 per night
CA $138
per night
Nov 29 - Nov 30
Stay at this guesthouse in Pittsfield. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Colonial Theater and Berkshire Museum are located nearby.
Pet-friendly
Parking included
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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 snow-covered town with buildings, a ski lift, and a mountain in the background.
Photo by Robin/Loving Life
Open Photo by Robin/Loving Life

Bousquet Ski Area

8.2/10 (48 reviews)
Hit the slopes at Bousquet Ski Area during your trip to Pittsfield. Wander the lakeside in this family-friendly 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 $1,065. 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.