Photo by Elizabeth Massa Peroulakis

Find hotels in Chester, MA from ฿2,431

    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
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Property class

Top 10 Chester hotels and places to stay

River Valley Inn

2.0 star property
8.8 out of 10, Excellent, (42)
"Great quiet motel. "
The price is ฿4,181
฿4,670 total
includes taxes & fees
31 Aug - 1 Sept
River Valley Inn

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
9.0 out of 10, Wonderful, (1003)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is ฿4,105
฿4,585 total
includes taxes & fees
4 Sept - 5 Sept
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
7.6 out of 10, Good, (546)
"Excellent location, friendly service, clean, comfortable room."
The price is ฿2,431
฿2,715 total
includes taxes & fees
11 Sept - 12 Sept
Travelodge by Wyndham Great Barrington Berkshires

D. Hotel Suites & Spa

3.0 star property
9.4 out of 10, Exceptional, (2228)
"Clean hotel, large room, comfortable bed, great breakfast"
The price is ฿3,983
฿4,628 total
includes taxes & fees
3 Sept - 4 Sept
D. Hotel Suites & Spa

Fairfield Inn & Suites Springfield Holyoke

2.5 star property
9.2 out of 10, Wonderful, (563)
"Great place in a great location."
The price is ฿3,954
฿4,417 total
includes taxes & fees
7 Sept - 8 Sept
Fairfield Inn & Suites Springfield Holyoke

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1004)
"Very clean rooms and excellent staff."
The price is ฿3,443
฿3,846 total
includes taxes & fees
1 Sept - 2 Sept
Best Western Plus Berkshire Hills Inn & Suites

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (787)
"My stay was perfect. I can't wait to stay there again. "
The price is ฿2,560
฿2,860 total
includes taxes & fees
1 Sept - 2 Sept
Howard Johnson by Wyndham Lenox

Element Lenox Berkshires

3.0 star property
9.6 out of 10, Exceptional, (4)
"New hotel very nice"
The price is ฿4,926
฿5,503 total
includes taxes & fees
4 Sept - 5 Sept
Element Lenox Berkshires

Monument Mountain Motel

2.5 star property
8.8 out of 10, Excellent, (744)
"A great mom & pop motel. Clean and friendly "
Monument Mountain Motel

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (599)
"Amazing place to stay. Can’t wait to go again. "
Berkshire Mountain Lodge

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1002)
"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."
The price is ฿4,138
฿5,890 total
includes taxes & fees
1 Sept - 2 Sept
The Cornell Inn, Lenox & The Berkshires

Blue - A Modern Hotel, Ascend Hotel Collection

2.5 star property
The price is ฿4,346
฿4,974 total
includes taxes & fees
4 Sept - 5 Sept
Blue - A Modern Hotel, Ascend Hotel Collection

Hampton Inn Hadley-Amherst Area

2.5 star property
9.0 out of 10, Wonderful, (931)
"Friendly staff."
The price is ฿4,432
฿4,950 total
includes taxes & fees
14 Sept - 15 Sept
Hampton Inn Hadley-Amherst Area

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (698)
"We needed a place to stay in the area Found the place cutely decorated and was happy there was a restaurant on premise "
The price is ฿5,207
฿5,816 total
includes taxes & fees
1 Sept - 2 Sept
Berkshires Untold

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1002)
"Great staff! Comfortable bed! "
The price is ฿4,656
฿5,201 total
includes taxes & fees
4 Sept - 5 Sept
Hampton Inn & Suites Berkshires-Lenox

Tru by Hilton Chicopee Springfield

2.5 star property
8.8 out of 10, Excellent, (1012)
"Clean, good breakfast options daily, great and helpful employees. "
The price is ฿3,968
฿4,502 total
includes taxes & fees
3 Sept - 4 Sept
Tru by Hilton Chicopee Springfield

Fairfield Inn & Suites Springfield Northampton/Amherst

3.0 star property
9.2 out of 10, Wonderful, (977)
"The place is amazing "
The price is ฿4,926
฿5,503 total
includes taxes & fees
7 Sept - 8 Sept
Fairfield Inn & Suites Springfield Northampton/Amherst

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.4 out of 10, Exceptional, (26)
"Do hotel, very clean we had a great day"
The price is ฿4,588
฿5,125 total
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (572)
"Fabulous place"
The price is ฿4,926
฿5,503 total
includes taxes & fees
1 Sept - 2 Sept
Courtyard by Marriott Lenox Berkshires

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (760)
"Quite and good location to around towns"
The price is ฿5,153
฿5,756 total
includes taxes & fees
24 Sept - 25 Sept
Hotel On North
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

Learn more about Chester

Experience the hiking, camping and riverfront in Chester!

Photo by Elizabeth Massa Peroulakis
Open Photo by Elizabeth Massa Peroulakis

Top Chester Hotel Reviews

More cheap stays in Chester

More cheap stays in Chester

Frequently asked questions

What's the best place to stay in Chester?

Berkshire Mountain Lodge, located 17.2 mi (27.7 km) from the heart of Chester, is a top choice for your stay, based on our traveller data. Other good choices for your visit to the area are Quality Inn West Springfield and La Quinta Inn & Suites by Wyndham Springfield MA. See all available top hotels, or vacation rentals in Chester.

If I need to cancel my hotel reservation in Chester, will I receive a refund?

Yes, the majority of room reservations are refundable if you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you have a reservation that's non-refundable, it may still be possible to cancel it and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Chester.

What is staying in Chester like?

Visitors can enjoy all that Chester has to offer, including the waterfalls, shopping and riverfront. Tourists can also enjoy the city's restaurants, theatres and monuments. In Chester, there are 2 hotels and other accommodation options to choose from. Find out more about Chester.

What is there to see in Chester?

A favourite place to visit is Chester Town Hall. You'll also find Glendale Falls and Pyramid Lake in the area. Take a look at what more there is to see and do in Expedia's Chester guide.

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.