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.
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Price was CA $1,002, price is now CA $868 per person
CA $868
per person
May 28 - May 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9/10 Wonderful! (858 reviews)
Was very clean and a great price
Reviewed on Apr 14, 2026
The Cornell Inn, Lenox & The Berkshires
Price was CA $1,482, price is now CA $1,188 per person
CA $1,188
per person
May 28 - May 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9/10 Wonderful! (1,001 reviews)
The breakfast was menu fresh and incredible. My brother ran into a medical emergency and the staff was super helpful and supportive.
Reviewed on Apr 13, 2026
The Ponds at Foxhollow
Price was CA $1,194, price is now CA $1,058 per person
CA $1,058
per person
May 28 - May 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.6/10 Excellent! (141 reviews)
Expedia stated the front desk is open until midnight, but when I arrived at 8:05pm the door to the registration bldg was locked.i located a mailbox marked “late check ins” where I found a key card that was only good for one of my two nights. It snowed 2-3” during my 2-day stay, but the sidewalks to my building were never shoveled. Room was extremely clean but quite outdated. Bathroom tiles were cracked with pieces missing along the exterior wall, allowing very cold air in. Price was good for my short stay - unfortunately I didn’t have time to use the clubhouse amenities.
Reviewed on Jan 7, 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 $118 per night from Apr 22 to Apr 23
CA $118
CA $147 total
Apr 22 - Apr 23
includes taxes & fees
8.8/10 Excellent! (2,335 reviews)
While this is a good value for the money for a one bedroom with separate kitchenette and living area, this is basically 2nd or 3rd rate for a timeshare unit. Couch is uncomfortable to sit on and bed isn't the best. Didn't provide some very basics, such as dish soap to wash dishes and pans which are ...
Reviewed on Apr 18, 2026
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
The price is CA $182 per night from May 19 to May 20
CA $182
CA $203 total
May 19 - May 20
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
Nice staff comfy bed nice views
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 $113 per night from Apr 21 to Apr 22
CA $113
CA $156 total
Apr 21 - Apr 22
includes taxes & fees
9/10 Wonderful! (907 reviews)
All clean staff great service
Reviewed on Apr 18, 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.
