Chester Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Elizabeth Massa Peroulakis
Top hotels in Chester
La Quinta Inn & Suites by Wyndham Springfield MA
100 Congress Street, Springfield, MA
Fully refundableReserve now, pay when you stay
The price is 3.138.744 ₫ per night from 14 Oct to 15 Oct
3.138.744 ₫
3.560.905 ₫ total
14 Oct - 15 Oct
includes taxes & fees
8/10 Very Good! (1,270 reviews)
"I believe you should clean the room daily and if I want to opt-out I could ask. You are calling lack of house cleaning GREEN is a joke. Everything is very clean, and the bar is a welcoming environment. The hot breakfast is good."
Reviewed on 1 Oct 2025
Red Roof Inn PLUS+ West Springfield
1254 Riverdale Street, West Springfield, MA
Fully refundableReserve now, pay when you stay
The price is 2.587.248 ₫ per night from 2 Nov to 3 Nov
2.587.248 ₫
2.961.106 ₫ total
2 Nov - 3 Nov
includes taxes & fees
6.8/10 (1,000 reviews)
"Great and what we expected. Clean Room. Awesome beds. Staff was polite. Bathrooms a bit outdated, but great stay for the price."
Reviewed on 28 Sept 2025
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is 2.458.309 ₫ per night from 2 Nov to 3 Nov
2.458.309 ₫
3.335.171 ₫ total
2 Nov - 3 Nov
includes taxes & fees
8.8/10 Excellent! (668 reviews)
"Nice room, bathroom could use some repair, crumbling sheetrock surrounding tub enclosure, priced well"
Reviewed on 30 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.
Popular places to visit
Chester Town Hall
You can get tickets for a performance at Chester Town Hall on your trip to Chester. Wander the lakeside and forests in this relaxing area.
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