4 Stars Hotels in Chester, Massachusetts from CA $138

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Check prices for these dates

Tonight
Nov 6 - Nov 7
Tomorrow
Nov 7 - Nov 8
This weekend
Nov 6 - Nov 8
Next weekend
Nov 13 - Nov 15

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.

1. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (434 reviews)
"Consistently, a clean, quiet, convenient location and comfortable stay."
United States
Debra
The price is CA $138
CA $155 total
includes taxes & fees
Nov 8 - Nov 9
The Central Downtown Inn & Suites
A large, white, multi-story house with a symmetrical design, surrounded by lush greenery and trees.

2. Seven Hills Inn

Seven Hills Inn
4.0 star property
Lenox
7.8 out of 10, Good, (467 reviews)
"Great location, nice breakfast and clean rooms"
United States
Christopher
Seven Hills Inn
A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

3. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (141 reviews)
"Wonderful location and hosts are amazing. Breakfast was great. Clean."
United States
Sebastien
The price is CA $516
CA $576 total
includes taxes & fees
Nov 17 - Nov 18
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.

4. Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (45 reviews)
"Comfortable bed. Quiet location. Excellent breakfast. Friendly host."
United States
Kathleen
The price is CA $321
CA $359 total
includes taxes & fees
Nov 11 - Nov 12
Hampton Terrace Inn
A cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.

5. 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
4.5 star property
Stockbridge
9.4 out of 10, Exceptional, (120 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is CA $507
CA $613 total
includes taxes & fees
Dec 6 - Dec 7
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A white two-story house with a front door, windows, and a chimney.

6. The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (96 reviews)
"Lovely property.unique historic buildings and rooms with updated amenities! Quiet and peaceful beautiful dinner!"
United States
mary ellen
The price is CA $405
CA $489 total
includes taxes & fees
Nov 8 - Nov 9
The Old Inn On The Green
A two-story white house with a front porch, a central entrance, and a small tower-like structure on the roof.

7. 33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (77 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
33 Main
A hotel room with a large bed, a flat-screen TV mounted on the wall, a bedside table with a mirror, a sink, and a sliding door leading to a bathroom.

8. Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (303 reviews)
"Staff wonderful, homemade breakfasts, outstanding experience!"
United States
Kathleen
Lakehouse Inn
Front of property

9. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.6 out of 10, Exceptional, (108 reviews)
"Wonderful place… clean, cosy room, comfy bed, friendly staff, great breakfast. Delightful location near Norman Rockwell museum."
United States
Kimberly
The price is CA $373
CA $438 total
includes taxes & fees
Nov 8 - Nov 9
The Inn at Stockbridge

Top Chester Hotel Reviews

A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.
Devonfield Inn B&B

Devonfield Inn B&B

Devonfield Inn B&B
Lee

10/10 Excellent

We stayed at the Devonfield Inn in mid-October during peak foliage season. The hotel is a wonderful historic home built in 1800 with much of its historic character preserved. Our hosts were so welcoming and made us feel at home. The room was very comfortable and breakfast was fantastic. In the morning, we got a special surprise to see a bear on the patio drinking from the fountain and robbing the bird feeder. Overall we highly recommend the Devonfield. We will definitely go back.
Canada
Lise
Reviewed October 17, 2019
Devonfield Inn B&B

Find out more about Chester

If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Chester are calling your name. Known for providing first-rate service in amazing locations, each of the Chester 4 Stars hotels lets discerning travelers bask in an unforgettable experience.

Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day.

It’s all waiting for you at the top four star hotels in Chester. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Chester, Massachusetts, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Chester hotels with 4 Stars provide everything you need to unwind in style.

Frequently Asked Questions

How much does it cost to stay in a 4-star hotel in Chester?

With Expedia's handy filter tool, scoring a fabulous deal on a 4-star hotel in Chester just got simpler. Start by entering your chosen arrival date and length of your escape. Then list the results by price and pick a hotel that best matches your style and budget.

  • Search for the lowest price from CA $138

What's the difference between 5-star and 4-star hotels in Chester?

If you choose to spend your vacation at a 4-star hotel in Chester, you'll usually find lots of conveniences to make sure you're comfortable, such as a pool, restaurant and gym. You can enjoy high-quality service and upmarket accommodations. Go for a 5-star hotel and you'll have access to a few more bells and whistles — think around-the-clock concierge, on-site spas and nightly turndown services. You'll most likely get extra amenities and exclusive services at a 5-star retreat, though both are terrific options for luxury travellers.

Does Chester have any 4-star all-inclusive resorts?

Enjoy a worry-free vacation experience where almost everything is included in the one upfront rate by using our "All inclusive" filter. Staying within budget is a cinch when your accommodations, meals and many activities are already taken care of. After more options? Browse the offers on Expedia's standard 4-star resorts in and around Chester too.

Are there any 4-star casino hotels in Chester?

Use our filter tool to refine your Chester search by star rating, amenities and more. Whether you're craving a complete casino resort experience or just want to give your luck a try while letting your hair down in 4-star style, you're sure to find a stay that strikes just the right balance between entertainment and relaxation.

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