Best Chester Hotels in 2026 from HK$544 - Fully Refundable Options

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Our top choices for Chester hotels

A hotel room with a sofa, armchair, desk with lamp, television, mini-fridge, and patterned carpet.

A hotel room with a bed, a desk, a television, a microwave, and a sofa.

A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.

1. Quality Inn Lee - Lenox South

Lee

Christine

HK$860

HK$961 total

includes taxes & fees

25 Oct - 26 Oct

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

A covered outdoor area with stone pillars and a view of a road and green hills.

An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.

2. Courtyard by Marriott Lenox Berkshires

Lenox

Tracy

HK$986

HK$1,101 total

includes taxes & fees

1 Nov - 2 Nov

A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

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

Great Barrington

Bruce

HK$1,127

HK$1,259 total

includes taxes & fees

2 Nov - 3 Nov

A hotel lobby with a reception desk, seating area, and a dining section.

A gym with treadmills, an elliptical, a stationary bike, and a bench press.

A modern dining area with tables and chairs, a patterned carpet, and a wall-mounted TV.

A snack and beverage display area with shelves stocked with chips and a refrigerated section with bottled water and soda.

4. Hampton Inn Westfield

Westfield

Shaleen

HK$934

HK$1,043 total

includes taxes & fees

1 Nov - 2 Nov

A modern hotel lobby with seating areas, tables, and a reception desk.

A coffee station with two coffee machines and a variety of coffee pods and cups.

A hotel room with two beds, a desk, a TV, and a window with curtains.

A breakfast area with a counter, coffee machine, and a display of pastries.

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

Great Barrington

Maria Dulce

HK$934

HK$1,043 total

includes taxes & fees

25 Oct - 26 Oct

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

A lakeside dock with kayaks and a covered boat ramp.

A dining area with large windows, wooden furniture, and a view of a lake.

A lodge with a large building and a dock by a lake, surrounded by forest.

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

Lee

Bob

HK$907

HK$1,013 total

includes taxes & fees

1 Nov - 2 Nov

A breakfast area with a waffle station, coffee machine, and various food options.

A fitness room with treadmills, an elliptical, and a stationary bike.

A modern hotel room with a large bed, a desk, and a chair.

7. Tru by Hilton Chicopee Springfield

Chicopee

SASHAWN

HK$860

HK$976 total

includes taxes & fees

1 Nov - 2 Nov

An indoor swimming pool with blue walls, large windows, and several lounge chairs.

A snack display with various packaged foods and a microwave.

A Hampton Inn hotel with a modern design, featuring a large entrance, a well-lit parking area, and multiple flags.

A hotel room with two beds, a desk, a chair, a TV, and a window with a view.

8. Hampton Inn Chicopee/Springfield

Chicopee

Melissa

HK$917

HK$1,040 total

includes taxes & fees

1 Nov - 2 Nov

A brick building with a green door, white porch chairs, and a pathway lined with pink flowers.

A hotel room with a bed, a sofa, a dining table, and a chair. There are two nightstands with lamps and a framed picture on the wall.

A modern hotel room with a dining area, a sofa, a bed, and a TV.

A modern hotel room with a bed, sofa, dining table, and chairs.

9. The Ellery

Northampton

Travis

HK$994

HK$1,110 total

includes taxes & fees

28 Oct - 29 Oct

A multi-story hotel with a prominent 'La Quinta' sign, featuring a symmetrical facade with evenly spaced windows and a central entrance.

An indoor swimming pool with clear blue water, surrounded by chairs and a high ceiling with visible ductwork.

A hotel room with two beds, a desk, a television, and a window with curtains.

A hotel dining area with multiple tables and chairs, a patterned carpet, and a reception desk in the background.

10. La Quinta Inn & Suites by Wyndham Springfield MA

Metro Center

Heather

HK$867

HK$984 total

includes taxes & fees

1 Nov - 2 Nov

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.

A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

11. The Yankee Inn

Lenox

William

HK$832

HK$929 total

includes taxes & fees

1 Nov - 2 Nov

A modern dining area with a high ceiling, large windows, and a mix of wooden and upholstered furniture.

A Quality Inn by Choice Hotels with a simple, modern design, featuring a prominent sign and a parking lot.

A modern hotel lobby with a reception desk, a coffee machine, a plant, a leather sofa, and a dining area.

A hotel room with a large bed, a chair, a nightstand with a phone, a wall-mounted light, and a window with curtains.

12. Quality Inn Westfield - Springfield

Westfield

Thomas

HK$734

HK$820 total

includes taxes & fees

1 Nov - 2 Nov

A Fairfield Inn & Suites by Marriott hotel with a modern design, a covered entrance, and landscaped areas.

An indoor swimming pool with clear signage, a no diving policy, and a seating area with chairs and a table.

A spacious lobby with a reception desk, a blue decorative wall, and a wooden floor.

A hotel lobby with a seating area, a bar, and a TV screen.

13. Fairfield Inn & Suites Springfield Holyoke

Holyoke

MONA

HK$1,027

HK$1,147 total

includes taxes & fees

25 Oct - 26 Oct

A patio area with a stone fire pit, wicker furniture, and a view of the building's interior.

A spacious hotel lobby with a high ceiling, a fireplace, seating areas, and a large TV screen.

A spacious lobby with comfortable seating, a fireplace, and large windows.

An indoor swimming pool with clear blue water, surrounded by lounge chairs and umbrellas.

14. Residence Inn Springfield Chicopee

Chicopee

Ronald

HK$1,327

HK$1,506 total

includes taxes & fees

25 Oct - 26 Oct

An outdoor patio area with seating, a fire feature, and a view of the building's exterior.

A modern reception area with a wooden reception desk, seating area with sofas and chairs, and large windows providing natural light.

A hotel room with two beds, a large window with a view of trees, and a wall mural.

A modern bar area with a long counter, multiple bar stools, and a wooden accent wall.

15. Courtyard by Marriott West Springfield

West Springfield

Amy

HK$1,029

HK$1,178 total

includes taxes & fees

1 Nov - 2 Nov

A laundry room with white appliances, green stools, and a colorful artwork on the wall.

A hotel room with a bed, two bedside tables with lamps, a nightstand, and a carpeted floor.

A hotel with a well-maintained garden and a sign indicating it is a Homewood Suites by Hilton.

A conference room with a rectangular table surrounded by chairs, large windows with curtains, and a patterned carpet.

16. Homewood Suites by Hilton Holyoke-Springfield/North

Holyoke

Andrew

HK$1,184

HK$1,322 total

includes taxes & fees

25 Oct - 26 Oct

A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.

A hotel patio with outdoor seating and a fire pit.

A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.

A spacious living room with a large sofa, a coffee table, and a fireplace.

17. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

HK$1,004

HK$1,121 total

includes taxes & fees

1 Nov - 2 Nov

A spacious hotel lobby with multiple seating areas, large windows, and a television.

A grocery store with shelves stocked with snacks and beverages, a refrigerated display case, and a wall with hexagonal patterns.

A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.

18. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

HK$907

HK$1,013 total

includes taxes & fees

3 Nov - 4 Nov

An indoor swimming pool with clear water, tiled floors, and a blue wall.

A snack bar with shelves of snacks and a refrigerated display.

A modern cafe with a counter, seating area, and large windows.

A modern hotel with a large entrance, multiple floors, and a well-lit facade.

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

Pittsfield

Sheldon

HK$894

HK$999 total

includes taxes & fees

20 Oct - 21 Oct

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

A garden with wooden Adirondack chairs and a stone pathway.

20. Berkshire Mountain Lodge

Pittsfield

Jay

HK$673

HK$927 total

includes taxes & fees

18 Oct - 19 Oct

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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 stone bridge over a flowing river with rocks and autumn foliage.

Top Chester Hotel Reviews

D. Hotel Suites & Spa

10/10 Excellent

"We came to town for a wedding at Northampton Union Station and it was a great location. The room was clean and the bed was comfortable."

Tru by Hilton Chicopee Springfield

10/10 Excellent

"The room was clean, it was spacious and the bed was really neat. The sheets did have a stain and I did tell them and they resolved it. The staff was super nice, at all times. Breakfast was delicious, one of the best hotel breakfast I had. There was different varieties of food. When something would run out, they would go fill back up quick."

Berkshire Mountain Lodge

8/10 Good

"I have stayed here multiple times. My unit this trip was very clean, well equipped and comfortable. The check in process and front desk staff were terrific. My only issue was a strong smell of marijuana coming through the slider and bedroom window . The staff gave me a fan to blow the smell back out however it was an issue throughout my stay."

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

10/10 Excellent

"Was only there for one night. But great hotel, room, staff, and breakfast."

La Quinta Inn & Suites by Wyndham Springfield MA

8/10 Good

"It was a nice property for the price."

Hotel On North

10/10 Excellent

"Delightful place with charm and warmth and character. I would love to come back."

Blue A Modern Hotel, an Ascend Collection Hotel

10/10 Excellent

"Near where my meetings were"

Quality Inn & Suites Northampton - Amherst

10/10 Excellent

"Excellent, great staff"

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"Wonderful resort"

More cheap stays in Chester

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

HK$487

HK$544 total

18 Oct - 19 Oct

includes taxes & fees

5.4/10 (911 reviews)

Quality Inn West Springfield

1150 Riverdale St West Springfield MA

HK$717

HK$821 total

30 Oct - 31 Oct

includes taxes & fees

Blue A Modern Hotel, an Ascend Collection Hotel

1080 Riverdale St West Springfield MA

HK$794

HK$908 total

25 Oct - 26 Oct

includes taxes & fees

9.2/10 Wonderful! (352 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

HK$832

HK$929 total

1 Nov - 2 Nov

includes taxes & fees

Quality Inn & Suites Northampton - Amherst

117 Conz St Northampton MA

HK$960

HK$1,073 total

25 Oct - 26 Oct

includes taxes & fees

7.2/10 Good! (1,001 reviews)

Hampton Inn West Springfield

1011 Riverdale St West Springfield MA

HK$959

HK$1,097 total

1 Nov - 2 Nov

includes taxes & fees

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.

What are some of the best holiday rentals that Chester has to offer?

Experience Three Sisters Sanctuary in Goshen, MA: This holiday home rental outside of Chester is equipped with a garden, air conditioning and a Smart TV to help you feel comfortable during your stay. See all 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.

Chester hotels from HK$544

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chester

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Chester hotels

1. Quality Inn Lee - Lenox South

2. Courtyard by Marriott Lenox Berkshires

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

4. Hampton Inn Westfield

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

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

7. Tru by Hilton Chicopee Springfield

8. Hampton Inn Chicopee/Springfield

9. The Ellery

10. La Quinta Inn & Suites by Wyndham Springfield MA

11. The Yankee Inn

12. Quality Inn Westfield - Springfield

13. Fairfield Inn & Suites Springfield Holyoke

14. Residence Inn Springfield Chicopee

15. Courtyard by Marriott West Springfield

16. Homewood Suites by Hilton Holyoke-Springfield/North

17. Hilton Garden Inn Lenox Pittsfield

18. Hampton Inn & Suites Berkshires-Lenox

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

20. Berkshire Mountain Lodge

Stay near popular Chester attractions

Chester Town Hall

Learn more about Chester

Top Chester Hotel Reviews

D. Hotel Suites & Spa

Tru by Hilton Chicopee Springfield

Berkshire Mountain Lodge

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

La Quinta Inn & Suites by Wyndham Springfield MA

Hotel On North

Blue A Modern Hotel, an Ascend Collection Hotel

Quality Inn & Suites Northampton - Amherst

Holiday Inn Club Vacations Oak 'n Spruce Resort

More cheap stays in Chester

FairBridge Inn Express

Quality Inn West Springfield

Blue A Modern Hotel, an Ascend Collection Hotel

The Yankee Inn

Quality Inn & Suites Northampton - Amherst

Hampton Inn West Springfield

Frequently asked questions

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