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 & Suites Albany-Downtown

Hampton Inn & Suites Albany-Downtown

2.5 out of 5
Downtown Albany
Price was CA $1,348, price is now CA $1,159 per person
CA $1,159
per person
Jul 10 - Jul 15
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.8/10 Excellent! (1,057 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

Hampton Inn Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
Price was CA $1,391, price is now CA $1,178 per person
CA $1,178
per person
Jul 10 - Jul 15
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.8/10 Excellent! (1,010 reviews)
Staff was great. Bathrooms could use a little upkeep.

Reviewed on May 1, 2026

Best Western Plus Franklin Square Inn Troy/Albany

Best Western Plus Franklin Square Inn Troy/Albany

2.5 out of 5
Price was CA $1,500, price is now CA $1,290 per person
CA $1,290
per person
Jul 10 - Jul 15
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.8/10 Excellent! (1,009 reviews)
Parking was safe Had to leave before breakfast

Reviewed on Apr 27, 2026

Hyatt Place Albany/Downtown

Hyatt Place Albany/Downtown

3 out of 5
Downtown Albany
Price was CA $1,454, price is now CA $1,259 per person
CA $1,259
per person
Jul 10 - Jul 15
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9/10 Wonderful! (1,599 reviews)
Amazing stay! No issues, I would definitely stay again!

Reviewed on May 7, 2026

Hilton Albany

Hilton Albany

3.5 out of 5
Downtown Albany
Price was CA $1,341, price is now CA $1,183 per person
CA $1,183
per person
Jul 10 - Jul 15
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
7.2/10 Good! (1,008 reviews)
Clean, convenient, comfortable.

Reviewed on May 3, 2026

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Pittsfield Hotel Deals

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is CA $120 per night from May 24 to May 25
CA $120
CA $164 total
May 24 - May 25
includes taxes & fees
9/10 Wonderful! (925 reviews)
Room very spacious and clean. Full kitchen is a great bonus.

Reviewed on May 4, 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 $204 per night from May 12 to May 13
CA $204
CA $228 total
May 12 - May 13
includes taxes & fees
9.6/10 Exceptional! (848 reviews)
Lovely “old” hotel, used to be a men’s clothing store, but it has been remodelled into an exceptional place to stay in downtown Pittsfield. Our room was huge, clean, comfy beds, nice sitting area, desk area, coffee/tea area, and shelves of books! The bathroom was huge, clean, and well-supplied. There ...

Reviewed on May 8, 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 $161 per night from May 17 to May 18
CA $161
CA $180 total
May 17 - May 18
includes taxes & fees
8/10 Very Good! (1,003 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.