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Chester Hotels from S$101

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Stay near popular Chester attractions

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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Learn more about Chester

Experience the hiking, camping and theatre in Chester!

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Frozen Sanderson Brook Falls in Chester
Photo by Elizabeth Massa Peroulakis
Open Photo by Elizabeth Massa Peroulakis

Top Chester Hotel Reviews

Hotel Northampton

Hotel Northampton

10/10 Excellent
"Great, gracious hotel with old time charm. Clean and comfortable too."
Philip 1-night trip
Posted 3 days ago
Hotel Northampton

More cheap stays in Chester

Riverdale Inn

Riverdale Inn

1500 Riverdale Street West Springfield MA
The price is S$101 per night from 3 Jan to 4 Jan
S$101
3 Jan - 4 Jan, 2026
includes taxes & fees
5.8/10 (999 reviews)

Frequently asked questions

What's the best place to stay in Chester?
D. Hotel Suites & Spa, located 19.1 mi (30.7 km) from the heart of Chester, is a top choice for your stay, based on our traveller data. Other good choices for your visit to the area are La Quinta Inn & Suites by Wyndham Springfield MA and Holiday Inn & Suites Pittsfield-Berkshires by IHG. See all available top hotels, or vacation rentals in Chester.
If I need to cancel my hotel reservation in Chester, will I receive a refund?
Yes, the majority of room reservations are refundable if you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you have a reservation that's non-refundable, it may still be possible to cancel it and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Chester.
What is staying in Chester like?
Visitors can enjoy all that Chester has to offer, including the waterfalls, shopping and riverfront. Tourists can also enjoy the city's restaurants, theatres and monuments. In Chester, there are 2 hotels and other accommodation options to choose from. Find out more about Chester.
What is there to see in Chester?
A favourite place to visit is Chester Town Hall. You'll also find Pyramid Lake and Blandford Ski Area in the area. Take a look at what more there is to see and do in Expedia's Chester guide.
What's the weather like in Chester?
The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Chester are January, February, November and March, with each month seeing an average of 15 cm of snowfall.

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