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.
Hampton Inn Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
Price was CA $1,533, price is now CA $1,273 per person
CA $1,273
per person
Jul 22 - Jul 28
found 6 hours ago
Roundtrip flight included
Edmonton (YEG) to Albany (ALB)
8.8/10 Excellent! (1,004 reviews)
Staff was great. Bathrooms could use a little upkeep.

Reviewed on May 1, 2026

Hilton Albany

Hilton Albany

3.5 out of 5
Downtown Albany
Price was CA $1,921, price is now CA $1,542 per person
CA $1,542
per person
Jul 22 - Jul 28
found 6 hours ago
Roundtrip flight included
Edmonton (YEG) to Albany (ALB)
7.2/10 Good! (1,004 reviews)
The Hilton hotel was cleaned I had a excellent experience I would recommend it

Reviewed on May 9, 2026

Hampton Inn & Suites Albany-Downtown

Hampton Inn & Suites Albany-Downtown

2.5 out of 5
Downtown Albany
Price was CA $1,885, price is now CA $1,513 per person
CA $1,513
per person
Jul 22 - Jul 28
found 6 hours ago
Roundtrip flight included
Edmonton (YEG) to Albany (ALB)
8.8/10 Excellent! (1,060 reviews)
We had to switch rooms due to a leaking shower. Somehow it was leaking into the room. Additionally the shower was “handicap” accessible but also sprayed water all over the bathroom floor. However they immediately moved us upon complaint.

Reviewed on Apr 20, 2026

Hyatt Place Albany/Downtown

Hyatt Place Albany/Downtown

3 out of 5
Downtown Albany
Price was CA $2,101, price is now CA $1,750 per person
CA $1,750
per person
Jul 22 - Jul 28
found 6 hours ago
Roundtrip flight included
Edmonton (YEG) to Albany (ALB)
9/10 Wonderful! (1,607 reviews)
clean rooms, good breakfast, friendly staff

Reviewed on May 11, 2026

La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area

La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area

3 out of 5
Price was CA $1,720, price is now CA $1,456 per person
CA $1,456
per person
Jul 22 - Jul 28
found 6 hours ago
Roundtrip flight included
Edmonton (YEG) to Albany (ALB)
8.6/10 Excellent! (1,079 reviews)
It was nice, room could have been cleaner. Fold old bar of soap in shower and hair in sink area and shower

Reviewed on May 13, 2026

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Pittsfield Hotel Deals

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is CA $120 per night from May 24 to May 25
CA $120
CA $165 total
May 24 - May 25
includes taxes & fees
9/10 Wonderful! (931 reviews)
These are all 1 bedroom suites. There was plenty of room in kitchen cupboards for our groceries. The kitchen was well supplied with cooking utensils, dishes and glassware. The location is excellent with several grocery stores and restaurants close by. Everything was perfect except for the height ...

Reviewed on May 11, 2026

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 $231 per night from May 17 to May 18
CA $231
CA $259 total
May 17 - May 18
includes taxes & fees
9.6/10 Exceptional! (850 reviews)
It was an absolute pleasure to stay! We enjoyed ourselves and felt very comfortable

Reviewed on May 11, 2026

Hotel On North
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Fully refundable
The price is CA $162 per night from May 27 to May 28
CA $162
CA $181 total
May 27 - May 28
includes taxes & fees
8/10 Very Good! (1,000 reviews)
Staff was nice. Room was clean. Parking lot was under construction. Had to park offsite. Wasn't a total inconvenience. One elevator was broken and the wait time was long each time we were trying to use.

Reviewed on Apr 19, 2026

Holiday Inn & Suites Pittsfield-Berkshires by IHG
See all 1,374 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.
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Discover the most popular places to visit in Pittsfield

Historic 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

Canoe Meadows Wildlife Sanctuary

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

Canoe Meadows Wildlife Sanctuary

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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.