Chester Vacation Packages

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Your Chester Vacation

Our vacation packages to Chester allow you to create your own adventure. Tailor your getaway to your needs and interests and make every moment count in this fantastic city. There's a whole load to see during a trip to Chester, including Becket Land Trust Historic Quarry and Chester Town Hall. Check out Expedia's wide range of travel options and book your ultimate vacation to Chester today.

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Chester Hotel Deals

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is CA $120 per night from May 24 to May 25
CA $120
CA $165 total
May 24 - May 25
includes taxes & fees
9/10 Wonderful! (931 reviews)
These are all 1 bedroom suites. There was plenty of room in kitchen cupboards for our groceries. The kitchen was well supplied with cooking utensils, dishes and glassware. The location is excellent with several grocery stores and restaurants close by. Everything was perfect except for the height ...

Reviewed on May 11, 2026

Berkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
The price is CA $137 per night from May 27 to May 28
CA $137
CA $153 total
May 27 - May 28
includes taxes & fees
9/10 Wonderful! (941 reviews)
Great experience

Reviewed on May 13, 2026

Berkshires Untold
Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St West Springfield MA
Fully refundable
The price is CA $134 per night from May 27 to May 28
CA $134
CA $154 total
May 27 - May 28
includes taxes & fees
7/10 Good! (1,011 reviews)
Breakfast on schedule ac worked the room was ok you could hear talking all night walls were like paper the balcony was dirty glass doors would not open easily and glass was dirty to housekeeping were more friendly better than the front desk Asian lady was a little hostile I won't go back there wasn't ...

Reviewed on May 12, 2026

Quality Inn West Springfield
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.