Photo by Elizabeth Massa Peroulakis

Chester Hotel Guide - 4 Stars Hotels in Chester, Massachusetts

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Top Chester 4 Star Hotels

Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4.0 star property
Pittsfield
8.6 out of 10, Excellent, (343)
"The rooms were large and well appointed! You could easily stay for a while and cook in the room. Nice balcony, nice living room area and very comfy bed and pillows. We enjoyed our stay very much"
United States
Candee
The price is Rp1.490.774
Rp1.665.227 total
includes taxes & fees
20 Nov - 21 Nov
The Central Downtown Inn & Suites
Porch
Lakehouse Inn

Lakehouse Inn

4.0 star property
Lee
9.6 out of 10, Exceptional, (288)
"Great Views & Hospitality"
United States
Gerald
The price is Rp2.873.037
Rp3.369.643 total
includes taxes & fees
16 Nov - 17 Nov
Lakehouse Inn
Business centre
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)
"It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!"
United States
Carol Anne
The price is Rp6.375.772
Rp7.712.873 total
includes taxes & fees
30 Nov - 1 Dec
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property
Seven Hills Inn

Seven Hills Inn

4.0 star property
Lenox
7.8 out of 10, Good, (467)
"Great location and grounds are really nice. "
United States
Angela
Seven Hills Inn
Room 191, 1 Queen Bed, 1 Single Bed, 1 Sofa Bed | Premium bedding, individually decorated, individually furnished
The Old Inn On The Green

The Old Inn On The Green

4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (90)
"2nd stay here, even nicer than the first (and the first was amazing!). Can’t wait to return to this enchanting inn! "
United States
Walter
The price is Rp5.091.670
Rp6.144.227 total
includes taxes & fees
16 Nov - 17 Nov
The Old Inn On The Green
Front of property – evening/night
Devonfield Inn B&B

Devonfield Inn B&B

4.0 star property
Lee
10.0 out of 10, Exceptional, (133)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
Exterior
The Inn at Stockbridge

The Inn at Stockbridge

4.0 star property
Lee
9.8 out of 10, Exceptional, (98)
"A first class little inn"
United States
Philip
The price is Rp4.192.624
Rp4.917.473 total
includes taxes & fees
18 Nov - 19 Nov
The Inn at Stockbridge
Exterior
Hampton Terrace Inn

Hampton Terrace Inn

4.0 star property
Lenox
9.0 out of 10, Wonderful, (42)
"Beautiful historic house in a great location. Responsive owner. Great visit!"
United States
Abby
The price is Rp4.388.853
Rp4.902.360 total
includes taxes & fees
17 Nov - 18 Nov
Hampton Terrace Inn
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)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is Rp7.996.426
Rp8.932.007 total
includes taxes & fees
24 Nov - 25 Nov
33 Main
Front of property – evening/night
Garden Gables Inn

Garden Gables Inn

4.0 star property
Lenox
9.2 out of 10, Wonderful, (57)
"Rosie the Innkeeper was very friendly and welcoming. The breakfast was outstanding and so was our waitress. Can’t wait to go back again. "
United States
john
Garden Gables Inn
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Frozen Sanderson Brook Falls in Chester
Photo by Elizabeth Massa Peroulakis
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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.

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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.