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.
Countryside Inn
Price was CA $852, price is now CA $787 per person
CA $787
per person
Sep 1 - Sep 3
found 3 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Albany (ALB)
7.6/10 Good! (352 reviews)
It’s a great room for the price. One woman does it all… I would stay here again.
Reviewed on Jun 20, 2026
Marriott Albany
Price was CA $1,385, price is now CA $1,297 per person
CA $1,297
per person
Aug 3 - Aug 6
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.4/10 Very good! (1,001 reviews)
Stayed here last minute. Not worth the ratings! Room was renovated but toilet ran all night and ceiling was all bubbling. I wouldn’t stay here again for the price point.
Reviewed on Jun 27, 2026
Ramada by Wyndham Cobleskill
Price was CA $886, price is now CA $838 per person
CA $838
per person
Sep 1 - Sep 3
found 3 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Albany (ALB)
9.2/10 Wonderful! (24 reviews)
The place is being remodeled and it's lot of mess all around in door and out door. Second breakfast was Continental not full service. But the rooms are big and new.
Reviewed on Jun 23, 2026
Pittsfield Hotel Deals
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is CA $199 per night from Jul 28 to Jul 29
CA $199
CA $254 total
Jul 28 - Jul 29
includes taxes & fees
9/10 Wonderful! (1,006 reviews)
"Spacious, clean and very comfortable suite! Beautiful nature view and lovely large pool all made the stay very relaxing. Staff was very welcoming and efficient. Will definitely stay there again. Thank you!"
Reviewed on Jun 28, 2026
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
Fully refundable
The price is CA $243 per night from Jul 6 to Jul 7
CA $243
CA $271 total
Jul 6 - Jul 7
includes taxes & fees
9.4/10 Exceptional! (117 reviews)
"Best hotel breakfast I have had in a long time. The breakfast attendant kept items well stocked. She made sure that vacated tables were cleaned and ready for the next guests to enjoy their meal. The room was kept very clean. I really enjoyed the fresh pancakes that were made to order by a pancake ..."
Reviewed on Jun 26, 2026
Hotel On North
297 North Street Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is CA $353 per night from Jul 7 to Jul 8
CA $353
CA $395 total
Jul 7 - Jul 8
includes taxes & fees
9.6/10 Exceptional! (869 reviews)
"Always a great experience at Hotel on North! Great, comfortable room with amazing bathroom. Helpful and friendly staff. Safe parking in the rear secured lot."
Reviewed on Jun 24, 2026
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
