Chester Hotel Guide - 4 Stars Hotels in Chester, Massachusetts

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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 Rp1.744.608
Rp1.948.659 total
includes taxes & fees
13 Apr - 14 Apr
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 Rp5.293.175
Rp6.403.362 total
includes taxes & fees
25 Apr - 26 Apr
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 Rp5.114.096
Rp5.712.394 total
includes taxes & fees
26 Apr - 27 Apr
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 Rp4.289.683
Rp5.031.313 total
includes taxes & fees
25 Apr - 26 Apr
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 Rp5.216.720
Rp6.295.127 total
includes taxes & fees
13 Apr - 14 Apr
The Old Inn On The Green
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi

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 Rp8.449.376
Rp9.437.954 total
includes taxes & fees
13 Apr - 14 Apr
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 Rp3.744.066
Rp4.182.099 total
includes taxes & fees
15 Apr - 16 Apr
Hampton Terrace Inn
Front of property – evening/night

Garden Gables

Garden Gables
4.0 star property
Lenox
Garden Gables
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Frequently asked questions

How much does it cost to stay in a 4-star hotel in Chester?
We can help you easily find the ideal 4-star hotel for your holiday in Chester. Use our handy filter tool to fine-tune your search by things like price, conveniences and property star rating and get access to terrific deals in a few clicks.

  • Search for the lowest price from Rp1.948.659

What's the difference between 5-star and 4-star hotels in Chester?
Treat yourself to luxury living during your Chester getaway by choosing a 4-star hotel. As well as featuring upscale accommodation, these retreats are typically packed with amenities such as bathrobes, large beds and more. A 5-star hotel will go the extra mile to make your stay an even more lavish and special one. Concierge assistance, elegant furnishings and world-class dining are only the start of the exclusive conveniences and services you'll likely have access to.
Does Chester have any 4-star all-inclusive resorts?
Enjoy a carefree holiday experience where everything is included in one upfront price by using our "All inclusive" filter. Keeping to your budget is a cinch when your accommodation, food and many activities are already taken care of. Eager for more ideas? Check out the terrific deals on Expedia's standard 4-star options in and around Chester too.