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.
Hampton Inn Albany-Wolf Road (Airport)
Price was CA $1,315, price is now CA $1,074 per person
CA $1,074
per person
Jun 28 - Jul 3
found 3 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
The Cornell Inn, Lenox & The Berkshires
Price was CA $2,976, price is now CA $2,089 per person
CA $2,089
per person
Jun 28 - Jul 3
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (1,004 reviews)
Lovely Inn , comfy bed and suite. The breakfast was delicious…especially enjoyed the frittata, fresh baked sweet breads, and latte. Appreciated the fireplace and cognac nightcap served on on a cool April evening ,coming back from a delicious dinner in Lenox. Kool speak easy style bar, good vibes!
Reviewed on May 1, 2026
Hideaway Inn Lenox
Price was CA $2,103, price is now CA $1,612 per person
CA $1,612
per person
Jun 28 - Jul 3
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
6/10 (1 review)
The room was comfortable and well done. There was no heat in our room with no control for the air unit. There was also a drip coming from the exhaust fan in the bathroom. We were only there one night so I didn't call for support.
Reviewed on Apr 16, 2026
Vacation Village in the Berkshires
Price was CA $1,337, price is now CA $1,105 per person
CA $1,105
per person
Jun 28 - Jul 3
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.8/10 Excellent! (2,342 reviews)
Muito bom para aproveitar em família ou a 2
Reviewed on May 3, 2026
Hancock Hotel Deals
Jiminy Peak Mountain Resort
37 Corey Rd Hancock MA
Fully refundableReserve now, pay when you stay
The price is CA $177 per night from May 18 to May 19
CA $177
CA $198 total
May 18 - May 19
includes taxes & fees
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Hancock MA
The price is CA $186 per night from May 13 to May 14
CA $186
CA $457 total
May 13 - May 14
includes taxes & fees
7.6/10 Good! (13 reviews)
We loved our stay at this well maintained condo! Owner was very helpful and polite. We will be renting again for sure!
Reviewed on Feb 23, 2026
Berkshire Mountain Lodge
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! (924 reviews)
Room very spacious and clean. Full kitchen is a great bonus.
Reviewed on May 4, 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.
