Photo by Elizabeth Massa Peroulakis

4 Star Hotels in Chester, Massachusetts

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Top Chester 4 Star Hotels

33 Main
Luxury Room, 1 King Bed, Bathtub
33 Main
4.0 star property
10.0 out of 10, Exceptional, (62)
"I love the fact that it only had eight rooms they had happy hour from 5 to 6 PM so we are able to meet other people at the hotel. I love the rooms and the cleanliness and especially the breakfast they were amazing and delicious!! I would recommend this hotel highly!"
The price is €401
per night
27 May - 28 May
33 Main
Devonfield Inn B&B
Front of property – evening/night
Devonfield Inn B&B
4.0 star property
10.0 out of 10, Exceptional, (106)
"The classic character of the Inn is so beautiful and adds to the whole experience!"
The price is €291
per night
5 May - 6 May
Devonfield Inn B&B
Lakehouse Inn
Aerial view
Lakehouse Inn
4.0 star property
9.6 out of 10, Exceptional, (150)
"Love this Inn, all employees were friendly and knowledgeable about things to do in the area. The breakfast was delicious . I look forward to staying at the Inn again."
The price is €148
per night
9 May - 10 May
Lakehouse Inn
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The Inn at Stockbridge
Exterior
The Inn at Stockbridge
4.0 star property
9.6 out of 10, Exceptional, (92)
"Great B&B with everything you need especially for a quick getaway to vist Stockbridge & Great Barrington Massachusetts. The new owners have added new touches to this Inn and the pride of ownership shows. Highly recommended 👌 "
The Inn at Stockbridge
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business centre
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
9.2 out of 10, Wonderful, (101)
"The b&b was so beautiful and unique! The area was serene. The host was very sweet and accommodating."
The price is €418
per night
5 May - 6 May
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Garden Gables Inn
Front of property – evening/night
Garden Gables Inn
4.0 star property
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. "
Garden Gables Inn
The Old Inn On The Green
Room 191, 1 Queen Bed, 1 Single Bed, 1 Sofa Bed
The Old Inn On The Green
4.0 star property
9.0 out of 10, Wonderful, (70)
"It was great experience. "
The price is €315
per night
9 May - 10 May
The Old Inn On The Green
Hampton Terrace Inn
Seasonal outdoor pool
Hampton Terrace Inn
4.0 star property
9.0 out of 10, Wonderful, (42)
"Beautiful historic house in a great location. Responsive owner. Great visit!"
Hampton Terrace Inn
The Central Downtown Inn & Suites
Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites
4.0 star property
8.6 out of 10, Excellent, (228)
"Everything was Great"
The Central Downtown Inn & Suites
Seven Hills Inn
Terrace/patio
Seven Hills Inn
4.0 star property
7.8 out of 10, Good, (467)
"Great breakfast, amazing property, comfortable beds! Water in shower wasn’t hot, had to take a “warm-cold” fast shower but it didn’t matter. The view, the quiet, nature and siting areas made the stay perfect. Will come again!!"
Seven Hills Inn