Cummington Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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Your Cummington Vacation

Take the stress out of planning your next epic adventure with a Cummington vacation package. Whether you're visiting for its food, history, art or other highlights, there's a never-ending supply of new experiences to be had. If seeing the sights is a priority during your trip to Cummington, make sure you stop by leading attractions like Chesterfield Gorge and Swift River. Browse Expedia's wide range of travel options and start organizing your dream vacation to Cummington now.

Top Cummington Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Lakeside Inn
Boston Harbor Hotel
Raffles Boston
Studio Allston Hotel
Sesuit Harbor House

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Cummington Hotel Deals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is CA $80 per night from Sep 11 to Sep 12
CA $80
CA $105 total
Sep 11 - Sep 12
includes taxes & fees
Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
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
8.8/10 Excellent! (598 reviews)
"The staff was friendly and helpful it was easy to get in and out and convenient to get around."

Reviewed on Aug. 27, 2025

Berkshire Mountain Lodge
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd, Holyoke, MA
Fully refundableReserve now, pay when you stay
The price is CA $169 per night from Sep 3 to Sep 4
CA $169
CA $196 total
Sep 3 - Sep 4
includes taxes & fees
D. Hotel Suites & Spa
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.