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Chester Hotels from S$89

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22 Sept - 23 Sept
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23 Sept - 24 Sept
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25 Sept - 27 Sept
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2 Oct - 4 Oct

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Our top choices for Chester hotels

A building with a flat roof, multiple windows, and a satellite dish.
A kitchen with wooden cabinets, a granite countertop, a stainless steel sink, and a coffee maker.
An outdoor patio with a table and chairs, surrounded by wooden deck and greenery.
A hotel room with a large bed, a chair, a nightstand with a lamp, and a window with blinds.

1. Becket Motel

Becket Motel
Becket
United States
Paul
S$192
includes taxes & fees
23 Sept - 24 Sept
Becket Motel
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

2. The Yankee Inn

The Yankee Inn
Lenox
United States
William
S$167
includes taxes & fees
28 Sept - 29 Sept
The Yankee Inn
A reception area with a fireplace, seating, and a doormat with the logo "Quality".
A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.
A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.
A hotel room with a bed, a desk, a television, a microwave, and a sofa.

3. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
Lee
United States
Wendy
S$156
includes taxes & fees
19 Oct - 20 Oct
Quality Inn Lee - Lenox South
A calm lake at dusk with a wooden dock and two chairs facing the water.
A lakeside dock with chairs and a table, surrounded by greenery and a clear sky.
A room with two beds, a round mirror, a red box, and a hanging light fixture.
A two-story house with a covered porch, a driveway, and a lawn with outdoor seating.

4. Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
United States
mike
S$210
includes taxes & fees
23 Sept - 24 Sept
Berkshire Lake Lodge
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
A lodge with a large building and a dock by a lake, surrounded by forest.
A lakeside lodge with a dock, fishing rods, and outdoor seating.
A lakeside dock with kayaks and a covered boat ramp.

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
Ann M
S$182
includes taxes & fees
28 Sept - 29 Sept
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A hotel lobby with a reception desk, seating area, and a dining section.
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.
A hotel room with two beds, a desk, a chair, a lamp, and a window with a view.

6. Hampton Inn Westfield

Hampton Inn Westfield
Westfield
United States
Mykola
S$175
includes taxes & fees
7 Oct - 8 Oct
Hampton Inn Westfield
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.
A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.
A hotel room with a dining area featuring a table and chairs, a kitchenette with a coffee machine, and a television on the wall.
A hotel room with a dining area, a sofa, a coffee station, and a TV mounted on the wall.

7. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
United States
COLLEEN
S$113
includes taxes & fees
23 Sept - 24 Sept
Howard Johnson by Wyndham Lenox
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A modern cafe with seating areas, a coffee station, and large windows offering a view of greenery.
A modern hotel with a large entrance, multiple floors, and a well-lit facade.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
United States
Susan
S$168
includes taxes & fees
20 Oct - 21 Oct
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.
A hotel room with a patterned carpet, a sofa, a chair, a small table, a lamp, a television on a cabinet, and two framed pictures on the wall.
A reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.
A reception area with grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.

9. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
Pittsfield
United States
Joe
S$151
includes taxes & fees
18 Oct - 19 Oct
Best Western Plus Berkshire Hills Inn & Suites
A modern dining area with a high ceiling, large windows, and a mix of wooden and upholstered furniture.
A hotel room with a large bed, a chair, a nightstand with a phone, a wall-mounted light, and a window with curtains.
A Quality Inn by Choice Hotels with a simple, modern design, featuring a prominent sign and a parking lot.
A modern office space with a large window overlooking a parking lot and trees.

10. Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
Westfield
United States
Thomas
S$139
includes taxes & fees
18 Oct - 19 Oct
Quality Inn Westfield - Springfield
A multi-story hotel with a prominent "Hotel Northampton" sign, featuring a classic architectural style with a brick facade and multiple windows.
A hotel lobby with a glass vase of white flowers on a table, red chairs, and a wooden reception desk.
A hotel room with a desk, chair, lamp, and a large mirror. There is a staircase leading to an outdoor area with a railing.
A hotel room with two beds, a TV, a desk, and a chair.

11. Hotel Northampton

Hotel Northampton
Northampton
United States
zane
S$176
includes taxes & fees
23 Sept - 24 Sept
Hotel Northampton
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.
A hotel room with a wooden dresser, a television, a microwave, and a mirror.
A row of white plastic chairs on a covered outdoor area with a white building in the background.
A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.

12. Monument Mountain Motel

Monument Mountain Motel
Great Barrington
United States
Victor
S$110
includes taxes & fees
23 Sept - 24 Sept
Monument Mountain Motel
A spacious hotel lobby with multiple seating areas, large windows, and a television.
A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.

13. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
United States
Larry
S$177
includes taxes & fees
29 Sept - 30 Sept
Hampton Inn & Suites Berkshires-Lenox
An outdoor patio with white chairs and tables, a central fire feature, and string lights.
A hotel with a sign reading "D. HOTEL & SUITES" on the facade.
A bar area with a wooden counter, bar stools, and a variety of bottles and glasses.
A bedroom with a four-poster bed, a leather sofa, a wooden coffee table, and a view of greenery through the window.

14. D. Hotel Suites & Spa

D. Hotel Suites & Spa
Holyoke
United States
Karen
S$182
includes taxes & fees
28 Sept - 29 Sept
D. Hotel Suites & Spa
A round wooden table with two wine glasses and a green bottle, set against a window with a view of a blue railing and trees.
A kitchenette with a refrigerator, coffee maker, toaster, and bread display.
A hotel reception desk with an orange counter, a computer, a beverage cooler, and framed awards on the wall.
A hotel room with a bed, a desk, and two wall-mounted lamps.

15. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
Lee
United States
Anna
S$99
includes taxes & fees
28 Sept - 29 Sept
Econo Lodge Lee - Great Barrington
A hotel room with two beds, a desk, a chair, a television, and a window with curtains.
A row of single-story motel buildings with a parking lot in front.
A bathroom with a toilet, a shower, and a towel rack.
A hotel room with two beds, a sofa, a desk, a TV, and a picture on the wall.

16. River Valley Inn

River Valley Inn
West Hatfield
United States
Michael
S$129
includes taxes & fees
23 Sept - 24 Sept
River Valley Inn
A clear blue swimming pool with a tiled edge and a few lounge chairs along the side.
A covered corridor with a metal railing, white walls, and a view of a street with parked cars.
A hotel room with two beds, a chair, and a bedside table with a phone.
A standard rectangular bathtub with a single faucet, tiled walls, and a geometric patterned floor.

17. Sunset Inn

Sunset Inn
Lee
United States
Lauren
S$118
includes taxes & fees
5 Oct - 6 Oct
Sunset Inn
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.
An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".
A cozy library with bookshelves, a fireplace, and comfortable seating.
A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.

18. Berkshires Untold

Berkshires Untold
Lenox
United States
Drue
S$199
includes taxes & fees
28 Sept - 29 Sept
Berkshires Untold
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 kitchenette with a microwave, coffee maker, and coffee cups.

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

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
United States
Maria Dulce
S$190
includes taxes & fees
19 Oct - 20 Oct
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.
A modern restaurant with wooden flooring, bar area, and seating arrangements.
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.
A covered outdoor area with stone pillars and a view of a road and green hills.

20. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
United States
Tracy
S$202
includes taxes & fees
27 Sept - 28 Sept
Courtyard by Marriott Lenox Berkshires
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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.
Photo by Chris Addams

Top Chester Hotel Reviews

D. Hotel Suites & Spa

D. Hotel Suites & Spa

10/10 Excellent
"Very convenient to Northampton, very clean and a beautiful property."
Matt 1-night trip
Posted 5 hours ago
D. Hotel Suites & Spa
Berkshires Untold

Berkshires Untold

8/10 Good
"Liked he cleanliness. Room was very cold and no heat was available."
Anne E 2-night trip
Posted 6 hours ago
Berkshires Untold
The Yankee Inn

The Yankee Inn

10/10 Excellent
"The room was spacious, clean and comfortable. I will definitely stay there again."
William 2-night trip
Posted 7 hours ago
The Yankee Inn
Hotel Northampton

Hotel Northampton

8/10 Good
"Nice place"
Quianna 1-night trip
Posted 11 hours ago
Hotel Northampton
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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

10/10 Excellent
"The room was clean and perfect when we arrived! The pool area was a big hit with my boys and the breakfast the next morning was amazing!"
Ruth 1-night trip
Posted 11 hours ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Riverdale Inn

Riverdale Inn

8/10 Good
"Nice rooms, fridge available, comfy beds and decent showers. Only problem is no elevator for 2nd floor. And heavy doors to go through. Friendly helpful staff. Decent price. Right on the P20 bus line. Lots of restaurants in the area and Holyoke Mall is like a 5-10 min bus ride from the hotel."
Karen 2-night trip
Posted 11 hours ago
Riverdale Inn
La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

10/10 Excellent
"It was great. One staff had an attitude but overall nice place to stay."
Fabiola 2-night trip
Posted 11 hours ago
La Quinta Inn & Suites by Wyndham Springfield MA
Blue A Modern Hotel, an Ascend Collection Hotel

Blue A Modern Hotel, an Ascend Collection Hotel

10/10 Excellent
"This was a great stay and the high tech massage chair was the cherry on top!"
Jiovanhi 1-night trip
Posted 11 hours ago
Blue A Modern Hotel, an Ascend Collection Hotel
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"This is a wonderful, historic inn. Check out the Red Lion Den for music. We heard a terrific local group. We ate in the Tavern and the food was tasty. This is not a luxurious place. It dates back to the 1700s. But it is really charming. My friends and I stayed in a suite in an out building. We had a low-ceiled living room downstairs, which was a. great place to talk and catch up. The bedroom situation was a little funky because the bathroom was right next to the bed in one of two sleeping areas upstairs and the door really squeaked when it opened and closed. But that was about our only complaint. I'd be delighted to return."
Gerald 1-night trip
Posted 13 hours ago
The Red Lion Inn

More cheap stays in Chester

FairBridge Inn Express

FairBridge Inn Express

16 Cheshire Road Pittsfield MA
S$89
5 Oct - 6 Oct
includes taxes & fees
FairBridge Inn Express
Quality Inn West Springfield

Quality Inn West Springfield

1150 Riverdale St West Springfield MA
S$133
18 Oct - 19 Oct
includes taxes & fees
7.2/10 Good! (1,009 reviews)
Quality Inn West Springfield
Blue A Modern Hotel, an Ascend Collection Hotel

Blue A Modern Hotel, an Ascend Collection Hotel

1080 Riverdale St West Springfield MA
S$148
18 Oct - 19 Oct
includes taxes & fees
9.2/10 Wonderful! (336 reviews)
Blue A Modern Hotel, an Ascend Collection Hotel
The Yankee Inn

The Yankee Inn

461 Pittsfield Rd Lenox MA
S$167
28 Sept - 29 Sept
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
The Yankee Inn
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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

1055 South Street Pittsfield MA
S$168
20 Oct - 21 Oct
includes taxes & fees
9.4/10 Exceptional! (216 reviews)
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Quality Inn & Suites Northampton - Amherst

Quality Inn & Suites Northampton - Amherst

117 Conz St Northampton MA
S$174
12 Oct - 13 Oct
includes taxes & fees
Quality Inn & Suites Northampton - Amherst

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 881 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 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 19ยฐC, while the coldest months are January and February, with an average of -2ยฐC. 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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