Photo by Elizabeth Massa Peroulakis

Find hotels in Chester, MA from 1.801.521 ₫

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
14 Jul - 15 Jul
Tomorrow
15 Jul - 16 Jul
This weekend
18 Jul - 20 Jul
Next weekend
25 Jul - 27 Jul

Filter by

Guest rating
Guest rating
Property class

Top 10 Chester hotels and places to stay

The Constance by the Lenox Collection
Situated in a tranquil setting, The Whittock offers a traditional home with a covered front porch and mature trees surrounding the property.

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (492)
"Had a fantastic stay, love this property. Cant wsit to go back"
The price is 4.431.742 ₫
4.950.257 ₫ total
includes taxes & fees
15 Jul - 16 Jul
The Constance by the Lenox Collection
The Yankee, Trademark Collection by Wyndham
Classic hotel entrance with a covered walkway, surrounded by beautifully maintained gardens.

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1013)
"Great service and a wonderful place to stay"
The price is 3.306.705 ₫
3.693.589 ₫ total
includes taxes & fees
24 Jul - 25 Jul
The Yankee, Trademark Collection by Wyndham
The Black Swan Lee - Lenox, Ascend Hotel Collection
Relax in a serene lakeside setting with Adirondack chairs and a tranquil atmosphere.

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1003)
"Beautiful location!"
The price is 4.673.511 ₫
5.220.312 ₫ total
includes taxes & fees
15 Jul - 16 Jul
The Black Swan Lee - Lenox, Ascend Hotel Collection
Berkshires Untold
Relax in a stylish space with a bar area, seating area, and large windows offering views of the outdoors.

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (632)
"Great place stay after an evening at Tanglewood!"
The price is 10.550.647 ₫
11.785.081 ₫ total
includes taxes & fees
25 Jul - 26 Jul
Berkshires Untold
The Cornell Inn, Lenox & The Berkshires
Traditional two-story house with a welcoming porch and balcony, set amidst snow-covered trees.

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1002)
"Breakfast each day was phenomenal, staff were all so friendly, hotel & room were beautifully decorated. We had a wonderful time & would stay here again!"
The price is 4.210.860 ₫
5.724.261 ₫ total
includes taxes & fees
21 Jul - 22 Jul
The Cornell Inn, Lenox & The Berkshires
Candlewood Suites West Springfield by IHG
Stylish hotel exterior with a central entrance and evenly spaced windows.

Candlewood Suites West Springfield by IHG

2.5 star property
8.4 out of 10, Very good, (731)
"A bit older facilities but otherwise meets all the basic needs and is easy on and off the 91 highway "
The price is 2.172.269 ₫
2.486.162 ₫ total
includes taxes & fees
27 Jul - 28 Jul
Candlewood Suites West Springfield by IHG
Econo Lodge Lee - Great Barrington
Relax in comfort with a large bed, two bedside tables, and a balcony with a view.

Econo Lodge Lee - Great Barrington

2.0 star property
6.2 out of 10, (608)
"It is clean and reasonably priced. We were comfortable and close to Tanglewood. "
The price is 1.664.449 ₫
1.859.190 ₫ total
includes taxes & fees
3 Aug - 4 Aug
Econo Lodge Lee - Great Barrington
Travelodge by Wyndham Great Barrington Berkshires
Relax in this inviting room with a large bed, flat-screen TV, and comfortable chair.

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
7.6 out of 10, Good, (532)
"The hotel was filled with cockroaches. We demanded another room and the same issue. Manager didn’t seem to be phased."
The price is 2.584.791 ₫
2.887.133 ₫ total
includes taxes & fees
17 Jul - 18 Jul
Travelodge by Wyndham Great Barrington Berkshires
Red Roof Inn PLUS+ West Springfield
Relax in style with comfortable seating and a convenient coffee station.

Red Roof Inn PLUS+ West Springfield

2.5 star property
7.0 out of 10, Good, (1003)
"Rooms were clean and the staff was nice. "
The price is 2.326.077 ₫
2.662.194 ₫ total
includes taxes & fees
20 Jul - 21 Jul
Red Roof Inn PLUS+ West Springfield
FairBridge Inn Express
Relax in a spacious room with a large bed, two bedside tables, and a separate bathtub area.

FairBridge Inn Express

2.5 star property
5.4 out of 10, (740)
"A total dump !"
The price is 1.856.350 ₫
2.073.577 ₫ total
includes taxes & fees
27 Jul - 28 Jul
FairBridge Inn Express
The Red Lion Inn
Relax by the serene pool surrounded by lounge chairs and umbrellas.

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1004)
"I had excellent stay at the Red Lion Inn "
The price is 4.934.601 ₫
6.678.499 ₫ total
includes taxes & fees
15 Jul - 16 Jul
The Red Lion Inn
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Dine in style with a long table set for a memorable meal, surrounded by cushioned chairs and large windows offering a view of the outdoors.

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (821)
"Very convenient location, downtown, short drive to local attractions "
The price is 3.002.535 ₫
3.353.832 ₫ total
includes taxes & fees
30 Jul - 31 Jul
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Play a round of golf amidst lush surroundings and scenic obstacles.

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

3.5 star property
9.0 out of 10, Wonderful, (673)
"We love this place. It's a wonderful location in the Berkshires, easy to get to all of the surrounding towns and attractions. The amenities are awesome, the units are spotless, and the service is friendly and prompt. Have stayed twice and cannot wait to return again!"
The price is 4.210.860 ₫
5.068.019 ₫ total
includes taxes & fees
23 Jul - 24 Jul
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Best Western Plus Berkshire Hills Inn & Suites
Welcome to our reception area, featuring a comfortable seating area, a reception desk, and a beautiful abstract art piece.

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1012)
"Very nice stay"
The price is 3.306.705 ₫
3.693.589 ₫ total
includes taxes & fees
27 Jul - 28 Jul
Best Western Plus Berkshire Hills Inn & Suites
Quality Inn West Springfield
Welcome to Quality Inn, where guests can check in and enjoy a warm atmosphere.

Quality Inn West Springfield

2.5 star property
7.0 out of 10, Good, (1007)
"Clean beds, great AC in room, good breakfast, pool was perfect. "
The price is 2.169.397 ₫
2.482.874 ₫ total
includes taxes & fees
27 Jul - 28 Jul
Quality Inn West Springfield
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Restful haven with a neatly made bed and a wooden headboard.

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
8.8 out of 10, Excellent, (636)
"Great place to stay. Excellent staff."
The price is 4.281.876 ₫
4.782.856 ₫ total
includes taxes & fees
20 Jul - 21 Jul
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Relax in a welcoming space with comfortable seating and a stunning chandelier.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.4 out of 10, Exceptional, (714)
"Nice outdoor seating areas, big pool, clean nicely appointed toom"
The price is 5.404.563 ₫
6.036.897 ₫ total
includes taxes & fees
17 Jul - 18 Jul
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Courtyard by Marriott Lenox Berkshires
Relax by the fire pit in our outdoor seating area, surrounded by wicker furniture under a covered patio with a flat roof.

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (564)
"After coming to Lenox for 15 years, I can easily say this is the best in town. "
The price is 5.978.961 ₫
6.678.499 ₫ total
includes taxes & fees
24 Jul - 25 Jul
Courtyard by Marriott Lenox Berkshires
Hotel On North
Enjoy a diverse menu at this restaurant, featuring a selection of drinks and a modern design.

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (743)
"Great boutique hotel"
The price is 4.934.601 ₫
5.511.949 ₫ total
includes taxes & fees
21 Jul - 22 Jul
Hotel On North
Howard Johnson by Wyndham Lenox
Stylish motel with a central entrance and two wings, featuring individual rooms with doors and windows.

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (754)
"Was great loved the jacuzzi tub "
The price is 2.584.791 ₫
2.887.133 ₫ total
includes taxes & fees
15 Jul - 16 Jul
Howard Johnson by Wyndham Lenox
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
Sign in
Sign up, it's free

Learn more about Chester

Experience the hiking, camping and waterfalls in Chester!

See all hotels in Chester
Photo by Elizabeth Massa Peroulakis
Open Photo by Elizabeth Massa Peroulakis

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.