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.
Park Manor Hotel

Park Manor Hotel

4 out of 5
per person
May 30 - Jun. 1
found 21 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Albany (ALB)
7.6/10 Good! (1,152 reviews)
Great place comfortable and jacuzzi is so nice

Reviewed on Mar. 2, 2025

Hampton Inn Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
per person
May 30 - Jun. 1
found 21 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Albany (ALB)
8.8/10 Excellent! (1,000 reviews)
Overall it was a decent hotel. They were redoing the tile in the lobby which made for quite a mess.

Reviewed on Mar. 3, 2025

The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Stockade Historic District
per person
May 30 - Jun. 1
found 21 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Albany (ALB)
9/10 Wonderful! (1,001 reviews)
Overall was a great staff and stay we had.The soft baked cookies were delicious.

Reviewed on Mar. 2, 2025

Homewood Suites By Hilton Schenectady

Homewood Suites By Hilton Schenectady

3 out of 5
per person
May 30 - Jun. 1
found 21 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Albany (ALB)
9/10 Wonderful! (969 reviews)
I like that they allow pets and the rooms are spacious

Reviewed on Feb. 9, 2025

The Albany Hotel

The Albany Hotel

2.5 out of 5
Downtown Albany
per person
May 30 - Jun. 1
found 21 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Albany (ALB)
6.8/10 (3 reviews)
We had an event at the MVP arena and it was 5 minute walk from there. We were happy with our stay. I wish they had a continental breakfast and expedia needs to update there pics because it shows they have a pool but the hotel took it out.

Reviewed on Mar. 2, 2025

Ready to book your vacation to Pittsfield?

 

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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 $150 per night from Mar. 8 to Mar. 9
CA $150
CA $168 total
includes taxes & fees
Mar 8 - Mar 9
7.8/10 Good! (743 reviews)
"Ruby is very helpful and friendly. Thank you!"

Reviewed on Feb. 26, 2025

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundable
The price is CA $172 per night from Mar. 16 to Mar. 17
CA $172
CA $221 total
includes taxes & fees
Mar 16 - Mar 17
8.8/10 Excellent! (427 reviews)
"Great central location for visits to multiple ski resorts."

Reviewed on Feb. 25, 2025

Berkshire Mountain Lodge
Hotel On North
Hotel On North
3.5 out of 5
297 North Street, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is CA $168 per night from Mar. 6 to Mar. 7
CA $168
CA $188 total
includes taxes & fees
Mar 6 - Mar 7
9.4/10 Exceptional! (686 reviews)
"Loved the ambience and the bar was very nice as well. The hotel provides coffee in the room and in the lobby. Wonderful bed and plenty of room. We will be back"

Reviewed on Mar. 1, 2025

Hotel On North
See all 1,308 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?
You can grab a vacation package to this popular destination from CA $1,088 on Expedia. But how much your vacation to Pittsfield costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Pittsfield?
January, March and April are the best times to search for cheap Pittsfield vacation packages. Traveling in less busy months means you can generally find lower prices on flights and hotels.
How many days is enough for Pittsfield?
Usually, a handful of days is enough to check out the major sights during your Pittsfield vacation. But if you prefer to have more time to kick back or take day trips, think about extending your itinerary.
Is it worth booking a vacation package to Pittsfield?
Pittsfield is a good vacation destination with attractions like Bousquet Ski Area among the many things to keep you busy. Whether you’re heading away with the family or planning a trip with friends, a Pittsfield vacation promises fun for everyone.
How to find the best Pittsfield package deals?
Landing a cheap Pittsfield package deal is a breeze with Expedia. After you’ve entered your destination and preferred dates under our “Packages” tab, set your budget range, apply a few filters and see what’s available. You can tailor your search by “Area,” “Amenities,” “Property type” and more. Sort the results by “Price: low to high” to discover the most wallet-friendly Pittsfield package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Pittsfield vacation as a package?
You can enjoy significant savings on your Pittsfield retreat by booking a personalized vacation package. Click on the “Package” heading, then enter your destination and travel dates to see the best airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Pittsfield?
If you have your Pittsfield travel dates finalized, book as soon as you can to score some unbeatable deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Pittsfield?

  1. Choose the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Pittsfield.
  2. Work out your budget: Make sure you have enough money to pay for everything from transportation and meals to flights and activities. Your hotel will probably be the biggest expense during your trip to Pittsfield.
  3. Decide how long to go for: Now that you know more about Pittsfield, you can work out the ideal length of your vacation. Create a draft plan and allocate enough time to cover everything you want to do.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that’s left is to choose a Pittsfield vacation package that brings all your bookings together.

Discover the most popular places to visit in Pittsfield

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

Canoe Meadows Wildlife Sanctuary

You can take time to visit Canoe Meadows Wildlife Sanctuary during your travels to Pittsfield. Wander the lakeside in this quaint area.

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