Chester Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Elizabeth Massa Peroulakis
- Plan, book, travel with confidence
- Better togetherSave up to NZ$616 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Chester Holiday
Our pick of the best Chester Hotel Deals
La Quinta Inn & Suites by Wyndham Springfield MA
100 Congress Street, Springfield, MA
Fully refundableReserve now, pay when you stay
The price is NZ$222 per night from 20 Nov to 21 Nov
NZ$222
20 Nov - 21 Nov
includes taxes & fees
8/10 Very Good! (1,296 reviews)
The location was convenient and in close proximity to my conference. Room was clean and spacious. Staff courteous, professional and friendly.
Reviewed on 12 Nov 2025
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (750 reviews)
Everything was so perfect for a weekend to just get away and decompress, the staff were great, the room was awesome.
Reviewed on 4 Nov 2025
Quality Inn West Springfield
1150 Riverdale St, West Springfield, MA
Fully refundableReserve now, pay when you stay
The price is NZ$170 per night from 26 Nov to 27 Nov
NZ$170
26 Nov - 27 Nov
includes taxes & fees
7/10 Good! (1,004 reviews)
The owner makes me feel like I am a personal friend of his and the best part of his day is when I walk in the door.
Reviewed on 7 Nov 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.
