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Cheap Chester hotels

D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
The price is AU$191 per night from 1 Jan to 2 Jan
AU$191
1 Jan - 2 Jan 2026
includes taxes & fees
With a stay at D. Hotel Suites & Spa in Holyoke, you'll be 4.6 mi (7.4 km) from Smith College and 10.4 mi (16.7 km) from University of Massachusetts ...
Opens in a new windowD. Hotel Suites & Spa
La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

3 out of 5
100 Congress Street Springfield MA
Fully refundableReserve now, pay when you stay
The price is AU$188 per night from 16 Dec to 17 Dec
AU$188
16 Dec - 17 Dec
includes taxes & fees
A stay at La Quinta Inn & Suites by Wyndham Springfield MA places you in the heart of Springfield, within a 5-minute drive of Paramount Theater and MGM ...
Opens in a new windowLa Quinta Inn & Suites by Wyndham Springfield MA
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Fully refundable
The price is AU$156 per night from 16 Dec to 17 Dec
AU$156
16 Dec - 17 Dec
includes taxes & fees
With a stay at Holiday Inn & Suites Pittsfield-Berkshires by IHG, you'll be centrally located in Pittsfield, within a 15-minute drive of Tanglewood Music Center ...
Opens in a new windowHoliday Inn & Suites Pittsfield-Berkshires by IHG
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The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is AU$126 per night from 24 Dec to 25 Dec
AU$126
24 Dec - 25 Dec
includes taxes & fees
Located in Lenox, The Yankee, Trademark Collection by Wyndham is a 4-minute drive from Bousquet Ski Area and 8 minutes from The Mount.
Opens in a new windowThe Yankee, Trademark Collection by Wyndham
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is AU$199 per night from 8 Jan to 9 Jan
AU$199
8 Jan - 9 Jan 2026
includes taxes & fees
With a stay at Berkshire Mountain Lodge in Pittsfield, you'll be next to a golf course, within a 10-minute drive of Tanglewood Music Center and Guido's ...
Opens in a new windowBerkshire Mountain Lodge
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Fully refundableReserve now, pay when you stay
The price is AU$319 per night from 14 Jan to 15 Jan
AU$319
14 Jan - 15 Jan 2026
includes taxes & fees
With a stay at The Red Lion Inn in Stockbridge, you'll be in the historical district, within a 15-minute drive of Tanglewood Music Center and Housatonic ...
Opens in a new windowThe Red Lion Inn
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is AU$184 per night from 15 Dec to 16 Dec
AU$184
15 Dec - 16 Dec
includes taxes & fees
Located in Lenox, Berkshires Untold is within a 10-minute drive of Shakespeare and Company and The Mount.
Opens in a new windowBerkshires Untold
Courtyard by Marriott West Springfield

Courtyard by Marriott West Springfield

3 out of 5
885 Riverdale Street West Springfield MA
Fully refundableReserve now, pay when you stay
The price is AU$203 per night from 21 Dec to 22 Dec
AU$203
21 Dec - 22 Dec
includes taxes & fees
When you stay at Courtyard by Marriott West Springfield in West Springfield, you'll be near the airport, within a 5-minute drive of Big E and Baystate Medical ...
Opens in a new windowCourtyard by Marriott West Springfield
Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

2.5 out of 5
440 Memorial Dr Chicopee MA
Fully refundableReserve now, pay when you stay
The price is AU$149 per night from 22 Dec to 23 Dec
AU$149
22 Dec - 23 Dec
includes taxes & fees
With a stay at Tru by Hilton Chicopee Springfield in Chicopee, you'll be within a 10-minute drive of MassMutual Center and MGM Springfield.
Opens in a new windowTru by Hilton Chicopee Springfield
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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.

Hotels in Chester, Springfield

Good days are those where the toughest decision you have to make is which hotel to book. And if you're planning to visit Chester, 40 kilometres from central Springfield, you have a pretty sweet range to select from!

No one will blame you if you want to spend your trip chilling out and sipping bevvies. But make sure you also find some time for Springfield's terrific attractions, such as the Naismith Memorial Basketball Hall of Fame and the Volleyball Hall of Fame.

If you and your mates are dying for some decent nosh but don't want to go too far away, why not try Classic Pizza? It's just a stone's throw away.

Accommodation options near Chester

You and your BFF having issues finding the right hotel in Chester? If so, you probably should think about venturing out a little further to Westfield, about 20 kilometres away. Our Westfield hotels guide has some good hotel options, including the Holiday Inn Express & Suites Westfield and Quality Inn Westfield - Springfield.

So, have a look at the Chester forecast, pack your favourite outfits and get a move on! You're just a couple of clicks away from wild nights and #TravelEnvy adventures!

Chester hotels essential information

Accommodation
842 hotels
Lowest Price
AU$126
Highest Price
AU$319
Popular hotels
D. Hotel Suites & Spa, La Quinta Inn & Suites by Wyndham Springfield MA, Holiday Inn & Suites Pittsfield-Berkshires by IHG, The Yankee, Trademark Collection by Wyndham, Berkshire Mountain Lodge, The Red Lion Inn, Berkshires Untold, Courtyard by Marriott West Springfield, Tru by Hilton Chicopee Springfield

Most recent Chester hotel reviews

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