A river flowing through a forest with autumn-colored trees.

Chester Hotels from S$113

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Check prices for these dates

This weekend
6 Nov - 8 Nov
Next weekend
13 Nov - 15 Nov

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Our top choices for Chester hotels

A Holiday Inn Express & Suites building with a clear entrance, a covered parking area, and a stone facade.

1. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (854 reviews)
"Always a pleasurable stay. The rooms are clean, the amenities are appreciated, and the staff very attentive. Great location and as a single traveler I always feel safe staying here."
United States
Cynthia
The price is S$119
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A reception area with a fireplace, seating, and a doormat with the logo "Quality".

2. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.6 out of 10, Excellent, (1,000 reviews)
"Perfect for a travel stop-over."
United States
James
The price is S$121
includes taxes & fees
2 Dec - 3 Dec
Quality Inn Lee - Lenox South
A lodge with a large building and a dock by a lake, surrounded by forest.

3. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,000 reviews)
"Amazing place, clean, staff is awesome , amazing location , amazing views! Free breakfast, free coffee bar , free gym and the best it’s pet friendly !"
United States
Gustavo
The price is S$155
includes taxes & fees
15 Nov - 16 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A brick building with a green door, white porch chairs, and a pathway lined with pink flowers.

4. The Ellery

The Ellery
3.5 star property
Northampton
9.4 out of 10, Exceptional, (1,006 reviews)
"great and quaint stay"
United States
Adalie
The price is S$148
includes taxes & fees
7 Dec - 8 Dec
The Ellery
Two Adirondack chairs facing a river with a forested hill in the background.

5. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"The location was good for our trip."
United States
Basil
The price is S$156
includes taxes & fees
20 Nov - 21 Nov
The Yankee Inn
A grassy area with a lake, trees, and red chairs arranged around a fire pit.

6. Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
9.8 out of 10, Exceptional, (27 reviews)
"excellent lakeside view"
United States
mike
The price is S$156
includes taxes & fees
13 Nov - 14 Nov
Berkshire Lake Lodge
A multi-story hotel with a classic facade, large windows, and a prominent entrance.

7. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (980 reviews)
"Very nice hotel"
United States
Philip
The price is S$166
includes taxes & fees
29 Nov - 30 Nov
Hotel On North
An outdoor patio with a table and chairs, surrounded by wooden deck and greenery.

8. Becket Motel

Becket Motel
2.5 star property
Becket
6.6 out of 10, (64 reviews)
"Comfortable stay "
United States
Paul
The price is S$200
includes taxes & fees
8 Nov - 9 Nov
Becket Motel
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

9. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (687 reviews)
"Great stay!"
United States
Vandhana
The price is S$179
includes taxes & fees
29 Nov - 30 Nov
Courtyard by Marriott Lenox Berkshires
A hotel lobby with a reception desk, seating area, and a dining section.

10. Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very good, (932 reviews)
"It was a good family hotel."
United States
Shaleen
The price is S$159
includes taxes & fees
7 Dec - 8 Dec
Hampton Inn Westfield
An indoor swimming pool with clear water, tiled floors, and a blue wall.

11. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (257 reviews)
"The room was clean and well kept, breakfast was amazing!"
United States
Ruth
The price is S$147
includes taxes & fees
6 Dec - 7 Dec
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Exterior

12. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,257 reviews)
"Comfortable stay, well stocked kitchen and room."
United States
Charline
The price is S$138
includes taxes & fees
6 Dec - 7 Dec
Berkshire Mountain Lodge
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

13. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.4 out of 10, Very good, (1,001 reviews)
"Room was spacious and clean"
United States
James
The price is S$133
includes taxes & fees
1 Dec - 2 Dec
Best Western Plus Berkshire Hills Inn & Suites
A hotel room with two beds, a desk, a chair, a television, and a window with curtains.

14. River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.4 out of 10, Very good, (305 reviews)
"Super friendly and helpful staff, convenient parking, decently sized room."
United States
Brandon
The price is S$121
includes taxes & fees
30 Nov - 1 Dec
River Valley Inn
A spacious hotel lobby with multiple seating areas, large windows, and a television.

15. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.0 out of 10, Wonderful, (1,000 reviews)
"Breakfast was great"
United States
Thomas
The price is S$157
includes taxes & fees
12 Nov - 13 Nov
Hampton Inn & Suites Berkshires-Lenox
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

16. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,066 reviews)
"Very nice place beautiful view"
United States
Brian
The price is S$150
includes taxes & fees
17 Nov - 18 Nov
Berkshires Untold
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

17. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (51 reviews)
"Clean, spacious room Accommodating staff especially Shawn and Jennifer at the front desk. Very nice pool and gym Definitely coming back"
United States
Francis
The price is S$193
includes taxes & fees
15 Nov - 16 Nov
Element by Marriott Lenox Berkshires
A modern lounge area with sofas, a pool table, and a unique chandelier.

18. Blue A Modern Hotel, an Ascend Collection Hotel

Blue A Modern Hotel, an Ascend Collection Hotel
2.0 star property
West Springfield
9.2 out of 10, Wonderful, (401 reviews)
"Overall great stay! Very helpful staff and the rooms were beautiful. I stayed alone and felt very comfortable."
United States
Samantha
The price is S$148
includes taxes & fees
26 Nov - 27 Nov
Blue A Modern Hotel, an Ascend Collection Hotel
A room with a round table and two chairs, a window with a view of trees and a building, and an air conditioning unit.

19. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (713 reviews)
"It was super clean and safe"
United States
Fernando
The price is S$80
includes taxes & fees
3 Dec - 4 Dec
Econo Lodge Lee - Great Barrington
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

20. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (820 reviews)
"Nice view and location for fall color."
United States
Md
The price is S$229
includes taxes & fees
12 Nov - 13 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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.
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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.
See properties

Learn more about Chester

Experience the hiking, camping and theatre in Chester!

See all hotels in Chester
A bridge over a calm river with trees and buildings in the background.

Top Chester Hotel Reviews

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

10/10 Excellent
"Ideally located near I90 Clean and spacious stay"
Shailendra 1-night trip
Posted 6 hours ago
Tru by Hilton Chicopee Springfield

More cheap stays in Chester

Quality Inn West Springfield

Quality Inn West Springfield

1150 Riverdale St West Springfield MA
The price is S$122 per night from 1 Dec to 2 Dec
S$122
1 Dec - 2 Dec
includes taxes & fees
7.2/10 Good! (1,008 reviews)

Frequently asked questions

What's the best place to stay in Chester?
Berkshire Mountain Lodge, located 17.2 mi (27.7 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 D. Hotel Suites & Spa and Hampton Inn West Springfield. 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. There are 887 hotels and other accommodation options in the surrounding area. 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 Glendale Falls and Pyramid Lake 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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