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

Compare and book 4 Star hotels in Chester, Massachusetts

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Check availability on Chester 4 Star Hotels

Tonight
13 Sept - 14 Sept
Tomorrow
14 Sept - 15 Sept
Next weekend
18 Sept - 20 Sept
In two weeks
25 Sept - 27 Sept

Our top choices for Chester 4-star hotels

A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.
A compact living space with a kitchenette, a dining area, and a sofa.
A hotel room with two beds, a nightstand with a lamp, and a window with curtains.
A modern apartment with a living room, kitchenette, and dining area.

1. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
United States
Rena
£81
includes taxes & fees
5 Oct - 6 Oct
The Central Downtown Inn & Suites
A living room with a fireplace, leather sofas, and a dog.
A stone fountain surrounded by trees in a park setting.

2. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
United States
Jodi
£327
includes taxes & fees
14 Sept - 15 Sept
The Inn at Stockbridge
A two-story house with a brick entrance and a white facade.
A neatly arranged bedroom with a bed, bedside table, and a dresser.
A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.
A cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.

3. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Stockbridge
United States
Philippe
£295
includes taxes & fees
28 Sept - 29 Sept
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A dining area with round tables set for two, a fireplace, and a mural on the wall.
A white two-story house with a front door, windows, and a chimney.
A cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.
A room with two brown leather armchairs, a wooden side table with a lamp, a potted plant, and a window with a view of a snowy landscape.

4. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
United States
Catherine
£294
includes taxes & fees
14 Sept - 15 Sept
The Old Inn On The Green
An indoor dining area with a central table and chairs, surrounded by a decorative archway and greenery.
A room with a large bay window, a wooden bench with cushions, and a chandelier.
A row of turquoise bicycles parked in front of a building with brown-framed windows and a white facade.
A large, white, multi-story house with a symmetrical design, surrounded by lush greenery and trees.

5. Seven Hills Inn

Seven Hills Inn
Lenox
United States
Christopher
Seven Hills Inn
A large, two-story house with a well-maintained lawn and a fence.
A bedroom with a large bed, a fireplace, a bathtub, and a window with a view of greenery.
A house with a fire pit in the yard, outdoor seating, and a large window overlooking the yard.
A dining area with a table set for two, a view of a green landscape through large windows, and outdoor seating with a view.

6. Devonfield Inn B&B

Devonfield Inn B&B
Lee
United States
Richard
£338
includes taxes & fees
14 Sept - 15 Sept
Devonfield Inn B&B
A white house with a balcony, green shutters, and a front door with a decorative glass panel. There are two large flower pots on the steps.
A room with a grand piano, a chessboard, a horse statue, and a blue armchair.
A grand staircase with red carpeted steps and a wooden handrail, leading to a landing with a vase of flowers and a framed picture.
A traditional living room with a fireplace, a grand piano, plush seating, and a bookshelf.

7. Hampton Terrace Inn

Hampton Terrace Inn
Lenox
United States
Kathleen
£182
includes taxes & fees
21 Sept - 22 Sept
Hampton Terrace Inn
A modern bathroom with a glass shower, white marble walls, and a large window.
A two-story white house with a front porch, a central entrance, and a small tower-like structure on the roof.
A room with a large bed, a chair, and a decorative hanging light fixture.
A breakfast buffet with pastries, fruits, and condiments.

8. 33 Main

33 Main
Lenox
United States
Tatyana
33 Main
A wooden deck with wicker furniture and a view of a lake.
A hallway with wooden flooring, a wooden bench, a vase with flowers, and a mirror on the wall.
A modern living room with a sofa, a coffee table, and a TV mounted on the wall.
A two-story house with a balcony, a front porch, and a well-maintained lawn.

9. Lakehouse Inn

Lakehouse Inn
Lee
United States
Kathleen
Lakehouse Inn
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A stone bridge over a flowing river with rocks and autumn foliage.
Photo by Chris Addams

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Frequently asked questions

How much does it cost to stay in a 4-star hotel in Chester?
Expedia can help you easily find the ideal 4-star hotel for your getaway in Chester. Use our filter tool to tailor your search by things like budget, conveniences and star rating and get access to unbeatable deals in a few clicks.
  • Search for the lowest price from £81
What's the difference between 5-star and 4-star hotels in Chester?
If you decide to book a stay at a 4-star hotel in Chester, you'll typically find loads of conveniences to ensure you're comfortable, such as a restaurant, gym and pool. You can enjoy top-quality service and upscale accommodation. Opt for a 5-star hotel and you'll have access to a few more perks — think on-site spas, concierge assistance and nightly turndown services. You're likely to get additional amenities and first-class services at a 5-star stay, though both are awesome options for luxury guests.
Does Chester have any 4-star all-inclusive resorts?
Finding holiday bliss in Chester is as easy as typing in your travel details and selecting our "All inclusive" filter. Stay and play where just about everything is already taken care of like your accommodation, meals and activities, or go for a standard 4-star resort in or around this much-loved destination.

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