Hancock Vacation Packages
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Your Hancock Vacation
When a city adventure is calling your name, answer it with a Hancock vacation package. With all your travel needs worked out before you leave, all you need to do here is focus on having the time of your life. Any trip to Hancock needs a well-planned itinerary. Fill yours with major attractions such as Jiminy Peak Mountain Resort, Pittsfield State Forest and Skyline Country Club. Whatever your travel plans or the size of your budget, organizing a tailored Hancock vacation is a walk in the park with Expedia.
Top Hancock Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Berkshire Mountain Lodge
Price was CA $632, price is now CA $524 per person
CA $524
per person
Aug 31 - Sep 3
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
9/10 Wonderful! (980 reviews)
Property very well maintained, everything you would need for an extended stay, we stayed one night for a show at Tanglewood(20” away) The rooms have microwave, fridge, dishes, dishwasher,etc. everything you would need to eat in. Also pool, hot tub, exercise and movies at night in a great room. Helpful staff, great price for a great room( separate dining area, living area, bedroom and huge bathroom!!!!!) extra clean woukd def go back
Reviewed on Jun 21, 2026
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Price was CA $743, price is now CA $621 per person
CA $621
per person
Aug 31 - Sep 3
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (910 reviews)
Mini golf was amazing, as was having access to shuffleboard, cornhole and more. And the arcade was great, too, we went back many times! Room was clean and nice with it's own balcony and the resort was calm and quiet.
Reviewed on Jun 19, 2026
Best Western Plus Berkshire Hills Inn & Suites
Price was CA $634, price is now CA $545 per person
CA $545
per person
Aug 31 - Sep 3
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
8.6/10 Excellent! (1,001 reviews)
The towels and bedding were very nice and the bed was comfortable. There was ample, close parking. However, the sink drain was slow. There was no body wash in the shower. The refrigerator noise was so loud we had to unplug it while we slept. The breakfast was poor (no fruit or meat) and the eggs & biscuits and gravy were barely warm. I would not recommend this hotel.
Reviewed on Jun 17, 2026
The Yankee Inn
Price was CA $693, price is now CA $597 per person
CA $597
per person
Aug 31 - Sep 3
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (1,016 reviews)
I had an excellent experience with the Yankee Inn. The room was updated and the house keeping was excellent. The location was good and the staff was very nice. The breakfast was very good. I would definitely recommend staying here.
Reviewed on Jun 23, 2026
Hancock Hotel Deals
Jiminy Peak Mountain Resort
37 Corey Rd Hancock MA
The price is CA $219 per night from Jul 7 to Jul 8
CA $219
CA $245 total
Jul 7 - Jul 8
includes taxes & fees
8.2/10 Very good! (999 reviews)
"Very nice ! Everything was ready , Country Store on property had a good selection on snacks, sandwiches , soups and quick items needed ."
Reviewed on Jun 21, 2026
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
The price is CA $218 per night from Jun 30 to Jul 1
CA $218
CA $243 total
Jun 30 - Jul 1
includes taxes & fees
8.8/10 Excellent! (1,008 reviews)
"No real breakfast"
Reviewed on Jun 21, 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
The price is CA $203 per night from Jul 7 to Jul 8
CA $203
CA $226 total
Jul 7 - Jul 8
includes taxes & fees
9.2/10 Wonderful! (1,005 reviews)
"I had an excellent experience with the Yankee Inn. The room was updated and the house keeping was excellent. The location was good and the staff was very nice. The breakfast was very good. I would definitely recommend staying here."
Reviewed on Jun 23, 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.
