Chester Packages (Flight + Hotel)
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Top hotels in Chester
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
The price is ฿3,956 per night from 6 May to 7 May
฿3,956
฿4,595 total
6 May - 7 May
includes taxes & fees
9.2/10 Wonderful! (2,218 reviews)
I’ll start with positives. The hotel was clean and the room was spacious and comfortable. Breakfast was very good and we liked that they changed the selection each day. The negatives, about an hour before we arrived with my elderly mother I received a text message informing me the only elevator was ...
Reviewed on 21 Apr 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is ฿2,526 per night from 28 Apr to 29 Apr
฿2,526
฿2,821 total
28 Apr - 29 Apr
includes taxes & fees
9/10 Wonderful! (908 reviews)
Nice, quite and friendly
Reviewed on 21 Apr 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is ฿2,632 per night from 26 Apr to 27 Apr
฿2,632
฿3,655 total
26 Apr - 27 Apr
includes taxes & fees
9/10 Wonderful! (911 reviews)
The rooms were beautiful and the kitchen had everything needed. The staff was SUPER friendly also. My kids loved the pool and the hot tub but mainly the hot chocolate which was free. It's like they died and went to cocoa heaven🤣 we will DEFINITELY be back to visit again. It was peaceful and quiet. ...
Reviewed on 21 Apr 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.
