Lodging Image

Chester hotels from RM273

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

Filter by

Property class

Guest rating

Selecting then applying a filter from this group will update the results on a new page

Our top choices for Chester hotels

A reception area with a fireplace, seating, and a doormat with the logo "Quality".

1. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.6 out of 10, Excellent, (1,006 reviews)
"Perfect for a travel stop-over."
United States
James
The price is RM379
RM423 total
includes taxes & fees
17 Nov - 18 Nov
Quality Inn Lee - Lenox South
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

2. 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, (1,014 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 RM448
RM501 total
includes taxes & fees
22 Nov - 23 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.

3. 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, (845 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 RM368
RM411 total
includes taxes & fees
12 Nov - 13 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

4. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (682 reviews)
"Great stay!"
United States
Vandhana
The price is RM513
RM573 total
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Lenox Berkshires
A Fairfield Inn & Suites by Marriott hotel with a modern design, a covered entrance, and landscaped areas.

5. Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (705 reviews)
"Super clean room, excellent temperature control wihh the the room a/c. Breakfast was hot and fresh, eggs, sausage, fruit, yogurts, oatmeal with all the toppings"
United States
Caroline
The price is RM500
RM559 total
includes taxes & fees
17 Nov - 18 Nov
Fairfield Inn & Suites Springfield Holyoke
Two Adirondack chairs facing a river with a forested hill in the background.

6. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,007 reviews)
"The location was good for our trip."
United States
Basil
The price is RM433
RM484 total
includes taxes & fees
1 Nov - 2 Nov
The Yankee Inn
A hotel lobby with a reception desk, seating area, and a dining section.

7. Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very good, (928 reviews)
"It was a good family hotel."
United States
Shaleen
The price is RM483
RM539 total
includes taxes & fees
17 Nov - 18 Nov
Hampton Inn Westfield
An indoor swimming pool with blue walls, large windows, and several lounge chairs.

8. Hampton Inn Chicopee/Springfield

Hampton Inn Chicopee/Springfield
2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1,003 reviews)
"Nice place, very comfy beds."
United States
Melissa
The price is RM452
RM513 total
includes taxes & fees
17 Nov - 18 Nov
Hampton Inn Chicopee/Springfield
A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.

9. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (715 reviews)
"Great place to stay. Great staff and convenient location. Nice restaurant as well."
United States
James
The price is RM485
RM542 total
includes taxes & fees
15 Nov - 16 Nov
Hilton Garden Inn Lenox Pittsfield
A brick building with a green door, white porch chairs, and a pathway lined with pink flowers.

10. The Ellery

The Ellery
3.5 star property
Northampton
9.4 out of 10, Exceptional, (1,010 reviews)
"This is a great stop. Nice beds, clean, and excellent breakfast."
United States
Travis
The price is RM518
RM578 total
includes taxes & fees
16 Nov - 17 Nov
The Ellery
A modern hotel building with a prominent 'tru' logo, multiple floors, and a covered entrance area.

11. Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield
2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1,008 reviews)
"Everything was wonderful- room, breakfast"
United States
Gary
The price is RM448
RM508 total
includes taxes & fees
3 Nov - 4 Nov
Tru by Hilton Chicopee Springfield
A building with a flat roof, multiple windows, and a satellite dish.

12. Becket Motel

Becket Motel
2.5 star property
Becket
6.6 out of 10, (64 reviews)
"Comfortable stay "
United States
Paul
The price is RM450
RM639 total
includes taxes & fees
29 Oct - 30 Oct
Becket Motel
An indoor swimming pool with clear water, tiled floors, and a blue wall.

13. 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, (247 reviews)
"This a much better Holiday Inn than the one at Saugerties that we went one day before."
United States
Yuguo
The price is RM388
RM434 total
includes taxes & fees
24 Nov - 25 Nov
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A modern dining area with a high ceiling, large windows, and a mix of wooden and upholstered furniture.

14. Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (1,000 reviews)
"Great place for the money. Would stay there again"
United States
Mark
The price is RM382
RM427 total
includes taxes & fees
22 Nov - 23 Nov
Quality Inn Westfield - Springfield
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

15. 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, (818 reviews)
"Nice view and location for fall color."
United States
Md
The price is RM587
RM656 total
includes taxes & fees
2 Nov - 3 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A modern lounge area with sofas, a pool table, and a unique chandelier.

16. 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, (385 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 RM413
RM473 total
includes taxes & fees
16 Nov - 17 Nov
Blue A Modern Hotel, an Ascend Collection Hotel
A multi-story hotel with a prominent "Hotel Northampton" sign, featuring a classic architectural style with a brick facade and multiple windows.

17. Hotel Northampton

Hotel Northampton
3.5 star property
Northampton
9.2 out of 10, Wonderful, (1,004 reviews)
"nice place to stay in the heart of downtown Northampton"
United States
Beth
The price is RM607
RM678 total
includes taxes & fees
28 Oct - 29 Oct
Hotel Northampton
Exterior

18. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,235 reviews)
"beautiful location, giant suite room for incredible value"
United States
Michael
The price is RM350
RM483 total
includes taxes & fees
22 Nov - 23 Nov
Berkshire Mountain Lodge
A multi-story hotel with a prominent 'La Quinta' sign, featuring a symmetrical facade with evenly spaced windows and a central entrance.

19. La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA
3.0 star property
Metro Center
8.0 out of 10, Very good, (1,259 reviews)
"This was a great hotel with clean rooms and a great breakfast."
United States
Heather
The price is RM451
RM512 total
includes taxes & fees
3 Nov - 4 Nov
La Quinta Inn & Suites by Wyndham Springfield MA
An outdoor patio area with seating, a fire feature, and a view of the building's exterior.

20. Courtyard by Marriott West Springfield

Courtyard by Marriott West Springfield
3.0 star property
West Springfield
9.2 out of 10, Wonderful, (699 reviews)
"Clean, comfy bed, great staff, great location to shops"
United States
Tyhesha
The price is RM536
RM613 total
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott West Springfield
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 snow-covered forest with a narrow stream running through it.
Photo by Elizabeth Massa Peroulakis
Open Photo by Elizabeth Massa Peroulakis

Top Chester Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

8/10 Good
"I love having a separate bedroom and a kitchen to make coffee in the morning. This is not my first time staying there, and every time the beds were uncomfortable. When you look at the bed, and there are 2 curves to the mattress where they have been slept in over time, you know it's going to be a tough night. The pillows were old as well. This is a typical timeshare where upgrades to furniture are few and far between. Other than that, it is a value for your money. And very convenient if you are a skier."
Barbara 4-night trip
Posted less than an hour ago
Berkshire Mountain Lodge

More cheap stays in Chester

Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield

1254 Riverdale Street West Springfield MA
The price is RM382 per night from 9 Nov to 10 Nov
RM382
RM438 total
9 Nov - 10 Nov
includes taxes & fees
7/10 Good! (1,005 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.

Explore a world of travel with Expedia