4 Stars Hotels in Chester, Massachusetts from CA $158

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Check availability on Chester 4 Star Hotels

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, (359 reviews)
"Clean room, easy checkin, loved the tea kettle. Clean, comfortable, would definitely return. "
United States
TIFFANY
The price is CA $141
CA $158 total
includes taxes & fees
Apr 13 - Apr 14
The Central Downtown Inn & Suites
Porch

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (297 reviews)
"Friendly staff, great location, beautiful views, cozy room."
United States
Elizabeth
Lakehouse Inn
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, (110 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is CA $428
CA $518 total
includes taxes & fees
Apr 24 - Apr 25
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, (137 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
The price is CA $414
CA $462 total
includes taxes & fees
Apr 14 - Apr 15
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)
"Well-run and elegant property. "
United States
Steven
The price is CA $347
CA $407 total
includes taxes & fees
Apr 24 - Apr 25
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 served; American cuisine

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 $422
CA $509 total
includes taxes & fees
Apr 13 - Apr 14
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 $629
CA $703 total
includes taxes & fees
Apr 19 - Apr 20
33 Main
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 $303
CA $338 total
includes taxes & fees
Apr 15 - Apr 16
Hampton Terrace Inn
Front of property - evening/night

Garden Gables

Garden Gables
4.0 star property
Lenox
Garden Gables
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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 $158

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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