Cheshire Vacation Packages
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Your Cheshire Vacation
When an adventure in the city is calling your name, answer it with a Cheshire vacation package. With all your travel needs taken care of before you go, all you have to do here is focus on enjoying yourself. Like to explore your new surroundings? Mount Greylock, Mount Greylock State Reservation and East Hoosac Quaker Meetinghouse are just a few of the best places to visit during a trip to Cheshire. Don't delay visiting this destination any longer. The ultimate Cheshire vacation is a few quick clicks away with Expedia.
Top Cheshire Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Clocktower Hotel Latham - North Albany, an Ascend Collection Hotel
Price was CA $795, price is now CA $713 per person
CA $713
per person
Jun 25 - Jun 29
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Albany (ALB)
8.6/10 Excellent! (1,010 reviews)
Staff was very friendly and welcoming. The breakfast was okay. The pool was on the colder side for being indoors.
Reviewed on Apr 5, 2026
Hilton Albany
Downtown Albany
Price was CA $949, price is now CA $802 per person
CA $802
per person
Jun 25 - Jun 29
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Albany (ALB)
7.2/10 Good! (1,005 reviews)
The hotel has a gorgeous location, modern renovation, relatively clean. But we noticed mice in the restaurant, there were not enough towels in the pool. But I liked the staff. In general, we are satisfied with the rest
Reviewed on Apr 5, 2026
Cheshire Hotel Deals
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is CA $144 per night from Apr 22 to Apr 23
CA $144
CA $176 total
Apr 22 - Apr 23
includes taxes & fees
8.8/10 Excellent! (2,327 reviews)
Did not used the pool but everything else was clean
Reviewed on Apr 7, 2026
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
The price is CA $193 per night from May 7 to May 8
CA $193
CA $216 total
May 7 - May 8
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
Indoor pool was great.
Reviewed on Apr 8, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is CA $137 per night from Apr 22 to Apr 23
CA $137
CA $184 total
Apr 22 - Apr 23
includes taxes & fees
9/10 Wonderful! (896 reviews)
Love that place. Does need a little sprucing up. Staff great and accomodating
Reviewed on Apr 5, 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.
