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Find 4 Star Hotels in Chester, MA from $111

Check availability on Chester 4 Star Hotels

Tonight
Oct 15 - Oct 16
Tomorrow
Oct 16 - Oct 17
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

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 covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.
A modern apartment with a living room, kitchenette, and dining area.
A compact living space with a kitchenette, a dining area, and a sofa.

1. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
United States
Rena
$99 nightly
$111 total
Oct 18 - Oct 19
Total with taxes and fees
The Central Downtown Inn & Suites
Front of property
A stone fountain surrounded by trees in a park setting.
Exterior
A living room with a fireplace, leather sofas, and a dog.

2. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
United States
Jodi
$383 nightly
$428 total
Nov 1 - Nov 2
Total with taxes and fees
The Inn at Stockbridge
A two-story house with a brick entrance and a white facade.
A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.
A neatly arranged bedroom with a bed, bedside table, and a dresser.
A dining area with tables set for a meal, surrounded by large windows offering a view of trees and a garden.

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
$393 nightly
$439 total
Nov 1 - Nov 2
Total with taxes and fees
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 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.
A cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.
A white two-story house with a front door, windows, and a chimney.

4. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
United States
Catherine
$319 nightly
$350 total
Nov 1 - Nov 2
Total with taxes and fees
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 dining room with a large wooden table, blue upholstered chairs, and a chandelier.
A row of turquoise bicycles parked in front of a building with brown-framed windows and a white facade.

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 dining area with a table set for two, a view of a green landscape through large windows, and outdoor seating with a view.
A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.
A bedroom with a large bed, a fireplace, a bathtub, and a window with a view of greenery.

6. Devonfield Inn B&B

Devonfield Inn B&B
Lee
United States
Sebastien
$369 nightly
$412 total
Nov 2 - Nov 3
Total with taxes and fees
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 traditional living room with a fireplace, a grand piano, plush seating, and a bookshelf.
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 room with a grand piano, a chessboard, a horse statue, and a blue armchair.

7. Hampton Terrace Inn

Hampton Terrace Inn
Lenox
United States
Kathleen
$219 nightly
$245 total
Nov 15 - Nov 16
Total with taxes and fees
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 neatly arranged bedroom with a large bed, a chair, and a window with a view of trees.

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

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Chester Four Star Hotel Information

When you need to book a room with luxurious amazing amenities and the best rates, the 4 star hotels in Chester, Massachusetts are incredible options. Known for their extra perks, first-rate service, and fantastic locations, each of the Chester 4 star hotels offers the ultimate experience for globe-trotting travelers. Relax in your expertly designed room. Kick back with around-the-clock room service.

Get a good night’s sleep with the ultra-plush bedding, and freshen up in the morning with designer-inspired body products. It’s all available when you stay at one of the top book a four star hotels in Chester. What’s more, thanks to Expedia you might even score a cheap great deal on a 4 star hotel in Chester, Massachusetts, areas near the hottest attractions, so you can plan a sightseeing adventure and take advantage of unbeatable discounts in one fell swoop.

Whether you’re putting together a serene getaway or want to revel in the most vibrant entertainment district, 4 star Chester hotels offer everything your heart desires.

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Chester?
To book a 4-star hotel in Chester that's within your budget, use Expedia's handy filter tool. Check out the available options during your getaway dates and use our pricing filter to set your limit. You can also list your results by the most wallet-friendly property first.
  • Search for the lowest price from $111
What's the difference between 5-star and 4-star hotels in Chester?
If you decide to spend your vacation at a 4-star hotel in Chester, you'll typically find plenty of amenities to keep you comfortable, such as a restaurant, gym and pool. You can experience high-quality service and deluxe accommodations. Pick a 5-star hotel and you'll get a few more bells and whistles — think on-site spas, around-the-clock concierge and indulgent turndown services. You're likely to get more amenities and exclusive services at a 5-star retreat, though both are fabulous options for luxury travelers.
Does Chester have any 4-star all-inclusive resorts?
Finding your dream resort in Chester is as easy as entering in your destination and dates, and clicking on our "All inclusive" filter. Stay and play where everything is already taken care of like your room, meals and activities, or go for a standard 4-star resort in or around this top destination.

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