Photo by Elizabeth Massa Peroulakis

Find hotels in Chester, MA from 1.840.360 ₫

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Star rating

Top 10 Chester hotels and places to stay

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
Lee
9.0 out of 10, Wonderful, (1004)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is 2.801.919 ₫
3.129.743 ₫ total
includes taxes & fees
16 Dec - 17 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1007)
"Great stay!"
United States
Ann
The price is 1.647.591 ₫
1.840.360 ₫ total
includes taxes & fees
7 Dec - 8 Dec
The Yankee, Trademark Collection by Wyndham

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (803)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is 2.443.261 ₫
2.729.123 ₫ total
includes taxes & fees
30 Nov - 1 Dec
Berkshires Untold

Candlewood Suites West Springfield by IHG

2.5 star property
West Springfield
8.4 out of 10, Very good, (786)
"Nice, friendly staff, clean room and comfortable suite.. highly recommend "
United States
Christopher
The price is 1.877.686 ₫
2.149.012 ₫ total
includes taxes & fees
30 Nov - 1 Dec
Candlewood Suites West Springfield by IHG

The Cornell Inn, Lenox & The Berkshires

3.5 star property
Lenox
9.0 out of 10, Wonderful, (1001)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is 3.396.585 ₫
4.824.959 ₫ total
includes taxes & fees
30 Nov - 1 Dec
The Cornell Inn, Lenox & The Berkshires

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very good, (970)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is 2.354.492 ₫
2.629.967 ₫ total
includes taxes & fees
29 Nov - 30 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1002)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is 4.008.392 ₫
5.655.525 ₫ total
includes taxes & fees
21 Dec - 22 Dec
The Red Lion Inn

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
South Lee
9.0 out of 10, Wonderful, (790)
"Place was great!"
United States
Benjamin
The price is 2.808.512 ₫
3.505.246 ₫ total
includes taxes & fees
30 Nov - 1 Dec
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (60)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is 2.510.614 ₫
2.804.356 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
Great Barrington
8.8 out of 10, Excellent, (698)
"Everything was wonderful....super clean rooms, check-in was fast and smooth, staff was on top of everything. We definitely will be back at Holiday Inn. "
United States
Tabitha
The price is 2.821.697 ₫
3.151.836 ₫ total
includes taxes & fees
11 Dec - 12 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Red Roof Inn PLUS+ West Springfield

2.5 star property
West Springfield
6.8 out of 10, (1004)
"Great like always "
United States
Sharee
The price is 2.183.519 ₫
2.499.038 ₫ total
includes taxes & fees
10 Dec - 11 Dec
Red Roof Inn PLUS+ West Springfield

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (765)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
Berkshire Mountain Lodge

River Valley Inn

2.0 star property
West Hatfield
8.6 out of 10, Excellent, (97)
"Clean room, comfortable bed, nice shower! Owners were very nice - we will definitely stay here again!"
United States
Deb
The price is 2.874.439 ₫
3.210.748 ₫ total
includes taxes & fees
1 Dec - 2 Dec
River Valley Inn

Chambery Inn

3.0 star property
Lee
9.6 out of 10, Exceptional, (373)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn

La Quinta Inn & Suites by Wyndham Springfield MA

3.0 star property
Metro Center
8.2 out of 10, Very good, (1305)
"Great staff, very clean property, and good breakfast. "
United States
Jasmine
The price is 2.913.996 ₫
3.305.929 ₫ total
includes taxes & fees
4 Dec - 5 Dec
La Quinta Inn & Suites by Wyndham Springfield MA

Hotel On North

3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (801)
"Clean room and staff was super friendly"
United States
Yuen
The price is 3.517.608 ₫
3.929.168 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Hotel On North

Quality Inn West Springfield

2.5 star property
West Springfield
7.0 out of 10, Good, (1019)
"Room and staff were good "
United States
George
The price is 2.222.548 ₫
2.543.706 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Quality Inn West Springfield

D. Hotel Suites & Spa

3.0 star property
Holyoke
9.4 out of 10, Exceptional, (2262)
"Very clean room, great variety of food at breakfast, friendly and helpful staff."
United States
Liz
The price is 2.254.059 ₫
2.618.521 ₫ total
includes taxes & fees
11 Dec - 12 Dec
D. Hotel Suites & Spa

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
Great Barrington
9.4 out of 10, Exceptional, (756)
"Clean room, very courteous staff "
United States
Thomas
The price is 3.982.021 ₫
4.447.918 ₫ total
includes taxes & fees
30 Nov - 1 Dec
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Courtyard by Marriott West Springfield

3.0 star property
West Springfield
9.2 out of 10, Wonderful, (570)
"Room was clean and staff was super friendly "
United States
Jessuca
The price is 3.115.734 ₫
3.565.957 ₫ total
includes taxes & fees
11 Dec - 12 Dec
Courtyard by Marriott West Springfield
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Chester attractions

Learn more about Chester

Experience the hiking, camping and forests in Chester!

Frozen Sanderson Brook Falls in Chester
Photo by Elizabeth Massa Peroulakis
Open Photo by Elizabeth Massa Peroulakis

Top Chester Hotel Reviews

More cheap stays in Chester

Hotels in Chester with star rating

Frequently asked questions

What's the weather like in Chester?
The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Chester are January, February, November and March, with each month seeing an average of 15 cm of snowfall.