Photo by Elizabeth Massa Peroulakis

Find hotels in Chester, MA from 1.844.451 ₫

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
    Sign in

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
12 Oct - 13 Oct
Tomorrow
13 Oct - 14 Oct
Next weekend
17 Oct - 19 Oct
In two weeks
24 Oct - 26 Oct

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
Exterior

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
9.0 out of 10, Wonderful, (1006)
"Great Indian restaurant in the hotel!"
The price is 2.798.625 ₫
3.126.064 ₫ total
includes taxes & fees
2 Nov - 3 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (754)
"Easy parking, great community spaces, beautiful decor! "
The price is 2.304.724 ₫
2.574.378 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Berkshires Untold
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1004)
"Great location, very clean!"
The price is 3.532.194 ₫
3.945.469 ₫ total
includes taxes & fees
2 Nov - 3 Nov
The Yankee, Trademark Collection by Wyndham
Red Roof Inn PLUS+ West Springfield
Lobby

Red Roof Inn PLUS+ West Springfield

2.5 star property
7.0 out of 10, Good, (1008)
"Great and what we expected. Clean Room. Awesome beds. Staff was polite. Bathrooms a bit outdated, but great stay for the price."
The price is 2.583.717 ₫
2.957.064 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Red Roof Inn PLUS+ West Springfield
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1005)
"Very friendly staff. "
The price is 3.363.091 ₫
4.786.334 ₫ total
includes taxes & fees
28 Oct - 29 Oct
The Cornell Inn, Lenox & The Berkshires
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (895)
"Excellent customer service and great rooms"
The price is 2.713.020 ₫
3.030.443 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
River Valley Inn
Basic Studio, 1 King Bed | Desk, laptop workspace, free WiFi, bed sheets

River Valley Inn

2.0 star property
8.6 out of 10, Excellent, (75)
"Great quiet motel. "
The price is 3.134.460 ₫
3.501.192 ₫ total
includes taxes & fees
9 Nov - 10 Nov
River Valley Inn
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Lobby sitting area

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.4 out of 10, Exceptional, (52)
"Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout"
The price is 3.139.728 ₫
3.506.908 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity

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

3.5 star property
9.0 out of 10, Wonderful, (752)
"The lodging was convenient to all the area attractions."
The price is 3.058.074 ₫
3.783.576 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Hotel On North
Front of property – evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (779)
"Great property! Very large clean room in a unique hotel! "
The price is 3.187.140 ₫
3.560.035 ₫ total
includes taxes & fees
3 Nov - 4 Nov
Hotel On North
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (692)
"Great stay, perfect "
The price is 2.454.954 ₫
3.330.621 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Berkshire Mountain Lodge
Candlewood Suites West Springfield by IHG
Exterior

Candlewood Suites West Springfield by IHG

2.5 star property
8.4 out of 10, Very good, (771)
"Nice, friendly staff, clean room and comfortable suite.. highly recommend "
The price is 2.581.320 ₫
2.954.320 ₫ total
includes taxes & fees
26 Oct - 27 Oct
Candlewood Suites West Springfield by IHG
La Quinta Inn & Suites by Wyndham Springfield MA
Indoor pool

La Quinta Inn & Suites by Wyndham Springfield MA

3.0 star property
8.2 out of 10, Very good, (1281)
"Affordable and easy access to the Big E. Friendly staff. "
The price is 3.000.126 ₫
3.403.644 ₫ total
includes taxes & fees
9 Nov - 10 Nov
La Quinta Inn & Suites by Wyndham Springfield MA
Travelodge by Wyndham Great Barrington Berkshires
In-room safe, desk, free cots/infant beds, free rollaway beds

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
7.6 out of 10, Good, (551)
"Excellent location, friendly service, clean, comfortable room."
The price is 1.975.500 ₫
2.206.765 ₫ total
includes taxes & fees
15 Oct - 16 Oct
Travelodge by Wyndham Great Barrington Berkshires
Quality Inn West Springfield
Check-in/check-out kiosk

Quality Inn West Springfield

2.5 star property
7.0 out of 10, Good, (1009)
"Convenient nice cozy hotel with breakfast included and spacious rooms. "
The price is 2.216.511 ₫
2.536.797 ₫ total
includes taxes & fees
26 Oct - 27 Oct
Quality Inn West Springfield
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
8.8 out of 10, Excellent, (674)
"Great place to have a girls night for old friends when one of us is back in town for a night. Very convenient place well kept. "
The price is 2.718.288 ₫
3.036.212 ₫ total
includes taxes & fees
10 Nov - 11 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Blue – A Modern Hotel, an Ascend Collection Hotel
Lobby

Blue – A Modern Hotel, an Ascend Collection Hotel

2.5 star property
9.4 out of 10, Exceptional, (35)
"Nice hotel"
The price is 3.335.961 ₫
3.818.007 ₫ total
includes taxes & fees
26 Oct - 27 Oct
Blue – A Modern Hotel, an Ascend Collection Hotel
Econo Lodge Lee - Great Barrington
Standard Room, 1 King Bed | Desk, iron/ironing board, free cots/infant beds, rollaway beds

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (635)
"Easy check in"
The price is 1.651.255 ₫
1.844.451 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Econo Lodge Lee - Great Barrington
D. Hotel Suites & Spa
Indoor pool

D. Hotel Suites & Spa

3.0 star property
9.4 out of 10, Exceptional, (2234)
"The staff is wonderful both at the hotel and dining ! "
The price is 2.894.674 ₫
3.362.679 ₫ total
includes taxes & fees
13 Oct - 14 Oct
D. Hotel Suites & Spa
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Lobby

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.4 out of 10, Exceptional, (743)
"The property is very nice and the staff was extremely friendly and helpful."
The price is 3.766.620 ₫
4.207.316 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Stay near popular Chester attractions

Chester Town Hall

You can get tickets for a performance at Chester Town Hall on your trip to Chester. Wander the lakeside and forests in this relaxing area.
See properties

Learn more about Chester

Experience the hiking, camping and theatre in Chester!

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

Top Chester Hotel Reviews

Blue - A Modern Hotel, Ascend Hotel Collection

Blue - A Modern Hotel, Ascend Hotel Collection

10/10 Excellent
"Very clean !"
Jay 1-night trip
Posted 4 days ago
Blue - A Modern Hotel, Ascend Hotel Collection

More cheap stays in Chester

Quality Inn West Springfield

Quality Inn West Springfield

1150 Riverdale St, West Springfield, MA
The price is 2.216.511 ₫ per night from 26 Oct to 27 Oct
2.216.511 ₫
2.536.797 ₫ total
26 Oct - 27 Oct
includes taxes & fees
7/10 Good! (1,005 reviews)

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.

Explore a world of travel with Expedia