Chester Packages (Flight + Hotel)
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Top hotels in Chester
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is ฿4,162 per night from 6 Jul to 7 Jul
฿4,162
฿5,382 total
6 Jul - 7 Jul
includes taxes & fees
9/10 Wonderful! (965 reviews)
"It is set off the road in the woods. Beautiful grounds with places to sit outside and relax. The rooms are big , clean, have full kitchens, and comfy beds. The magic coffee machine in the lobby makes great coffee for free and is always open to use. The pool is large and great and the outdoor hot ..."
Reviewed on 6 Jun 2026
Quality Inn West Springfield
1150 Riverdale St West Springfield MA
Fully refundable
The price is ฿3,039 per night from 28 Jun to 29 Jun
฿3,039
฿3,478 total
28 Jun - 29 Jun
includes taxes & fees
7/10 Good! (1,006 reviews)
"One of the best places we ever stayed. Loved the indoor pool and breakfast. Staff was great. Shampoo and conditioner in Shower was very convenient. Shower water pressure excellent only thing is mattress are a little hard but if you have to sleep on a hard mattress then this place is Golden. Gas station/Convince ..."
Reviewed on 2 Jun 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
The price is ฿3,647 per night from 25 Jun to 26 Jun
฿3,647
฿4,074 total
25 Jun - 26 Jun
includes taxes & fees
9.2/10 Wonderful! (1,005 reviews)
"I thought everything about the Yankee Inn was a cut or two above the motel experience -- except the breakfast, which was typical bland motel breakfast food. Tasteless scrambled eggs, bagels that any good store would be ashamed to sell. But everything else about the facilities was excellent."
Reviewed on 6 Jun 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.
