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 White House Inn
Price was CA $1,683, price is now CA $1,416 per person
CA $1,416
per person
Oct 12 - Oct 17
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (220 reviews)
The room we stayed in was comfortable and had a great view from the balcony. The bed was very comfortable.
I would have liked more space in the bathroom to put a cup and other things. Also, an exhaust fan would be nice in the bathroom. But it was pretty.
The staff were all very gracious.
We had a good meal Sunday night in the restaurant and our waiter was very nice. I knew that the restaurant would not be open on Monday and Tuesday, but it would have been nice to have the bar open for drinks on the patio in the evening on those nights.
Reviewed on Jul. 24, 2025
Aspen At Manchester
Price was CA $1,175, price is now CA $1,077 per person
CA $1,077
per person
Oct 12 - Oct 15
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.8/10 Excellent! (582 reviews)
Quiet, clean rooms very convenient to town center and the green mountain bluegrass festival. Would definitely stay here again.
Reviewed on Aug. 15, 2025
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 $147 per night from Sep 11 to Sep 12
CA $147
CA $180 total
Sep 11 - Sep 12
includes taxes & fees
Hotel Downstreet, Ascend Hotel Collection
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is CA $212 per night from Sep 17 to Sep 18
CA $212
CA $237 total
Sep 17 - Sep 18
includes taxes & fees
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is CA $106 per night from Sep 7 to Sep 8
CA $106
CA $149 total
Sep 7 - Sep 8
includes taxes & fees
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.