Chester Hotels from €62 - 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 modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.

A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.

1. Quality Inn Lee - Lenox South

Lee

Lucinda

€93

includes taxes & fees

5 Nov - 6 Nov

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

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.

A lakeside lodge with a dock, fishing rods, and outdoor seating.

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

Lee

Gustavo

€114

includes taxes & fees

15 Nov - 16 Nov

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.

A dining area with a round table set for four, surrounded by dark chairs. A white door is visible in the background, leading to a kitchen area with white appliances.

A hotel room with a large bed, a chair, a nightstand with a lamp, and a window with blinds.

3. Becket Motel

Becket

€140

includes taxes & fees

18 Oct - 19 Oct

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

A kitchenette with a microwave, coffee maker, and coffee cups.

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

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

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

Great Barrington

Maria Dulce

€89

includes taxes & fees

15 Nov - 16 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.

5. The Yankee Inn

Lenox

Basil

€106

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a bed, a desk, and two wall-mounted lamps.

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, two bedside tables, a desk, two chairs, and a large window with a view of greenery.

A motel with a parking lot, a signboard, and a lawn with plants.

6. Econo Lodge Lee - Great Barrington

Lee

Anna

€65

includes taxes & fees

6 Nov - 7 Nov

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.

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

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

7. Courtyard by Marriott Lenox Berkshires

Lenox

Vandhana

€126

includes taxes & fees

1 Nov - 2 Nov

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 motel rooms with red doors, a covered walkway, and a view of mountains in the background.

A row of white plastic chairs on a covered outdoor area with a white building in the background.

8. Monument Mountain Motel

Great Barrington

Andrea

€60

includes taxes & fees

1 Nov - 2 Nov

A calm lake at dusk with a wooden dock and two chairs facing the water.

A small, modern room with a desk, chair, and a flat-screen TV mounted on the wall.

A lakeside dock with chairs and a table, surrounded by greenery and a clear sky.

A two-story house with a covered porch, a driveway, and a lawn with outdoor seating.

9. Berkshire Lake Lodge

Lee

mike

€142

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

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 multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.

A gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.

10. Howard Johnson by Wyndham Lenox

Lenox

Aleksandr

€79

includes taxes & fees

8 Nov - 9 Nov

A building with a porch and multiple windows, surrounded by purple flowers.

A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

A living room with a sofa, armchair, coffee table, and a patterned rug.

A café with a display case, a frozen food section, and a marketplace sign.

11. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

South Lee

Michael

€134

includes taxes & fees

26 Oct - 27 Oct

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

A gym with exercise equipment including treadmills, a stationary bike, and free weights.

A room with a blue armchair, a wooden cabinet with a coffee maker, a television on the wall, and a small table with a cup.

A hotel room with a bed, a desk, a chair, and a carpeted floor.

12. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

€110

includes taxes & fees

1 Nov - 2 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 hotel with a large entrance, multiple floors, and a well-lit facade.

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

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

Pittsfield

Ginger

€99

includes taxes & fees

12 Nov - 13 Nov

A hotel room with a large bed, a desk with a coffee maker, a chair, a TV, and a window with curtains.

A motel with a two-story structure, multiple rooms with red doors, and a central staircase.

A living room with a patterned carpet, two sofas, a dining table, and chairs.

A hotel room with a sofa, a wooden table, a lamp, a telephone, and a painting on the wall.

14. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Mark

€79

includes taxes & fees

18 Oct - 19 Oct

A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

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.

A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.

An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".

15. Berkshires Untold

Lenox

Madhavi R

€130

includes taxes & fees

9 Nov - 10 Nov

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

A spacious lobby with a fireplace, seating area, and a bar.

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

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

16. Berkshire Mountain Lodge

Pittsfield

Joel

€105

includes taxes & fees

9 Nov - 10 Nov

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 grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.

A reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.

17. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

James

€93

includes taxes & fees

1 Nov - 2 Nov

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

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

18. Hampton Inn Westfield

Westfield

Shaleen

€118

includes taxes & fees

1 Nov - 2 Nov

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

A hotel room with two beds, a sofa, a desk, a TV, and a picture on the wall.

A row of single-story motel buildings with a parking lot in front.

A bathroom with a toilet, a shower, and a towel rack.

19. River Valley Inn

West Hatfield

Michael

€84

includes taxes & fees

1 Nov - 2 Nov

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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 snow-covered forest with a narrow stream running through it.

Top Chester Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Clean room - great linens- very welcoming- great choices for breakfast- superior coffee, hot chocolate, latte machine. Great value for the price we paid."

Berkshire Mountain Lodge

10/10 Excellent

"The bath tub and the wash basin had some water clogging"

Red Roof Inn PLUS+ West Springfield

10/10 Excellent

"The hotel was close everything very nice Clean staff was accommodating"

The Red Lion Inn

10/10 Excellent

"Wonderful"

Hotel On North

10/10 Excellent

"The hotel is charming in the heart of Pittsfield. The rooms were large and clean. It’s a great boutique hotel with 35 rooms. There is a restaurant attached to the hotel that had great food and drinks! Will definitely be back."

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

10/10 Excellent

"New hotel with clean"

Hampton Inn West Springfield

8/10 Good

"Room was clean, microwave and refrigerator clean and working, staff was friendly and helpful. Breakfast was better than most. The bath however had problems. The water faucet was loose and not connected to the tub and the water control was difficult to pull to start. Tub plug was very hard to use."

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"Nice place to stay"

Quality Inn West Springfield

10/10 Excellent

"Overall I had a great two day stay at the Quality Inn. I have stayed here over a dozen times when in the area to visit Six Flags, my previous visit was in the spring, and they have made some updates since! I noticed new chairs in the hallways and room, and the exterior of the building was repainted a new color and looks more modern! I had room 421, a 2 queen, which was mostly clean and comfortable. Only issue was the new tan chair by the door looked comfortable, but I did not sit in it, as it had long hairs and sticky residue all over the cushion... Otherwise the room was clean, beds were comfortable with 4 pillows on each bed, lots of towels, and fridge worked great! The lamp between the bed did not work though... At check in, the man with tattoos on his hands wasn't that friendly or welcoming but did honor my request for a higher floor. Later, when returning from dinner next door (Great Japanese restaurant!) I heard him tell a guest she had the entire 5th floor to herself, which was annoying as each night I had neighbors who I could hear easily through the walls... Why not space out guests when there is space? I woke up my first morning to hearing the neighbors talk... Breakfast was fine with a decent variety, I liked the donuts, eggs were decent, as was the sausage. The room was a great value and I will return. It looks like the first floor was restored for guest use again too! Nice to see some changes and hope they continue renovating and updating the property!"

More cheap stays in Chester

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

€62

10 Nov - 11 Nov

includes taxes & fees

5.4/10 (924 reviews)

Quality Inn West Springfield

1150 Riverdale St West Springfield MA

€91

8 Nov - 9 Nov

includes taxes & fees

The Yankee Inn

461 Pittsfield Rd Lenox MA

€106

1 Nov - 2 Nov

includes taxes & fees

Blue A Modern Hotel, an Ascend Collection Hotel

1080 Riverdale St West Springfield MA

€110

25 Oct - 26 Oct

includes taxes & fees

9.2/10 Wonderful! (366 reviews)

Quality Inn & Suites Northampton - Amherst

117 Conz St Northampton MA

€122

8 Nov - 9 Nov

includes taxes & fees

7.2/10 Good! (1,000 reviews)

Hampton Inn West Springfield

1011 Riverdale St West Springfield MA

€130

1 Nov - 2 Nov

includes taxes & fees

8.2/10 Very good! (1,002 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.

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

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

3. Becket Motel

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

5. The Yankee Inn

6. Econo Lodge Lee - Great Barrington

7. Courtyard by Marriott Lenox Berkshires

8. Monument Mountain Motel

9. Berkshire Lake Lodge

10. Howard Johnson by Wyndham Lenox

11. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

12. Hampton Inn & Suites Berkshires-Lenox

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

14. Travelodge by Wyndham Great Barrington Berkshires

15. Berkshires Untold

16. Berkshire Mountain Lodge

17. Best Western Plus Berkshire Hills Inn & Suites

18. Hampton Inn Westfield

19. River Valley Inn

Stay near popular Chester attractions

Chester Town Hall

Learn more about Chester

Top Chester Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Berkshire Mountain Lodge

Red Roof Inn PLUS+ West Springfield

The Red Lion Inn

Hotel On North

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

Hampton Inn West Springfield

Holiday Inn Club Vacations Oak 'n Spruce Resort

Quality Inn West Springfield

More cheap stays in Chester

FairBridge Inn Express

Quality Inn West Springfield

The Yankee Inn

Blue A Modern Hotel, an Ascend Collection Hotel

Quality Inn & Suites Northampton - Amherst

Hampton Inn West Springfield

Frequently asked questions

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