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.
Vacation Village in the Berkshires
Price was CA $1,213, price is now CA $1,030 per person
CA $1,030
per person
Jul 14 - Jul 17
found 5 hours ago
Roundtrip non-stop flight included
St. John's (YYT) to Albany (ALB)
8.8/10 Excellent! (2,355 reviews)
Everything was great
Room staff kitchen and pool . It was a quiet and peaceful stay
Reviewed on May 23, 2026
The Yankee Inn
Price was CA $1,388, price is now CA $1,156 per person
CA $1,156
per person
Jul 14 - Jul 17
found 5 hours ago
Roundtrip non-stop flight included
St. John's (YYT) to Albany (ALB)
9.2/10 Wonderful! (1,007 reviews)
Excellent value, I had a great experience. The breakfast was a cut above, but they didn't include any fresh fruit. Maybe that's nit-picking. I'd recommend it, especially to families. Lots of good restaurants nearby.
Reviewed on May 23, 2026
Berkshire Mountain Lodge
Price was CA $1,231, price is now CA $1,042 per person
CA $1,042
per person
Jul 14 - Jul 17
found 5 hours ago
Roundtrip non-stop flight included
St. John's (YYT) to Albany (ALB)
9/10 Wonderful! (928 reviews)
The stay was great . No complains at all . Definitely will be staying in the near future .
Reviewed on May 22, 2026
Berkshires Untold
Price was CA $1,406, price is now CA $1,198 per person
CA $1,198
per person
Jul 14 - Jul 17
found 5 hours ago
Roundtrip non-stop flight included
St. John's (YYT) to Albany (ALB)
9/10 Wonderful! (938 reviews)
Loved my stay here! The staff is friendly and helpful and the property is clean, comfortable and nicely appointed with a small bar and dining area. My room was spotless with an updated and spacious bathroom. The bed and linens were comfortable and there was a cozy reading chair as well. I loved the thoughtful decorative nods to the Berkshires and its history throughout. My only suggestion would be an adjustable desk chair as it was pretty low.
Reviewed on May 23, 2026
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Price was CA $1,221, price is now CA $1,076 per person
CA $1,076
per person
Jul 14 - Jul 17
found 5 hours ago
Roundtrip non-stop flight included
St. John's (YYT) to Albany (ALB)
9.2/10 Wonderful! (894 reviews)
Wonderful stay for families.
Reviewed on May 22, 2026
Cheshire Hotel Deals
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is CA $121 per night from May 25 to May 26
CA $121
CA $166 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (946 reviews)
"The stay was great . No complains at all . Definitely will be staying in the near future ."
Reviewed on May 22, 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from May 26 to May 27
CA $173
CA $193 total
May 26 - May 27
includes taxes & fees
9/10 Wonderful! (957 reviews)
"Loved my stay here! The staff is friendly and helpful and the property is clean, comfortable and nicely appointed with a small bar and dining area. My room was spotless with an updated and spacious bathroom. The bed and linens were comfortable and there was a cozy reading chair as well. I loved the ..."
Reviewed on May 23, 2026
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is CA $119 per night from May 26 to May 27
CA $119
CA $148 total
May 26 - May 27
includes taxes & fees
8.8/10 Excellent! (2,363 reviews)
"Everything was great Room staff kitchen and pool . It was a quiet and peaceful stay"
Reviewed on May 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.
