4 Stars Hotels in Chester, Massachusetts from CA $176

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Check availability on Chester 4 Star Hotels

This weekend
Jun 5 - Jun 7
Next weekend
Jun 12 - Jun 14

Our top choices for Chester 4-star hotels

Exterior

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (368 reviews)
"Easy access to parking, nearby everything and room was very clean. Definitely will come back here to stay again! "
United States
Aisha
The price is CA $157
CA $176 total
includes taxes & fees
Jun 7 - Jun 8
The Central Downtown Inn & Suites
Suite, Private Bathroom (RedBird Suite) | View from room

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
9.2 out of 10, Wonderful, (111 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is CA $455
CA $551 total
includes taxes & fees
Jun 23 - Jun 24
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property - evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (138 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is CA $469
CA $524 total
includes taxes & fees
Jun 8 - Jun 9
Devonfield Inn B&B
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Great spot close to town. Cozy, tasteful, comfortable room. Nice breakfasts and pleasant interaction with the staff. We love the Berkshires and we’ll definitely stay here again."
United States
Stephen
The Inn at Stockbridge
Front of property

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
Breakfast, lunch, dinner and brunch served

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (91 reviews)
"Beautiful Inn and outstanding chef"
United States
Catherine
The price is CA $455
CA $549 total
includes taxes & fees
Jun 3 - Jun 4
The Old Inn On The Green
Luxury Room, 1 King Bed, Bathtub

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is CA $809
CA $904 total
includes taxes & fees
Jun 3 - Jun 4
33 Main
Porch

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (299 reviews)
"Staff wonderful, homemade breakfasts, outstanding experience!"
United States
Kathleen
Lakehouse Inn
Exterior detail

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (44 reviews)
"Comfortable bed. Quiet location. Excellent breakfast. Friendly host."
United States
Kathleen
The price is CA $408
CA $456 total
includes taxes & fees
Jun 6 - Jun 7
Hampton Terrace Inn
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Learn more about Chester

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Photo by Chris Addams
Open Photo by Chris Addams

Top Chester Hotel Reviews

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 $176

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.

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