Chester Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Elizabeth Massa Peroulakis
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Save up to NZ$616 when you book a flight and hotel together*
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Chester Holiday
Our pick of the best Chester Hotel Deals
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is NZ$219 per night from 28 Sept to 29 Sept
NZ$219
28 Sept - 29 Sept
includes taxes & fees
8.8/10 Excellent! (656 reviews)
"Clean and spacious one bedroom suite with well stocked kitchen. Large indoor pool and outdoor year round Jacuzzi are wonderful. Also very affordable. Second time staying here and will stay here again."
Reviewed on 25 Sept 2025
La Quinta Inn & Suites by Wyndham Springfield MA
100 Congress Street, Springfield, MA
Fully refundableReserve now, pay when you stay
The price is NZ$234 per night from 29 Sept to 30 Sept
NZ$234
29 Sept - 30 Sept
includes taxes & fees
8/10 Very Good! (1,286 reviews)
"Friendly staff. Room smelled like cigarette smoke upon entering, but room spray resolved that. Bathtub was extreslow to drain, causing water to accumulate."
Reviewed on 25 Sept 2025
Red Roof Inn PLUS+ West Springfield
1254 Riverdale Street, West Springfield, MA
Fully refundableReserve now, pay when you stay
The price is NZ$175 per night from 2 Oct to 3 Oct
NZ$175
2 Oct - 3 Oct
includes taxes & fees
6.8/10 (1,018 reviews)
"."
Reviewed on 22 Sept 2025
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.
More holiday ideas
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
