Photo by Elizabeth Massa Peroulakis

Find hotels in Chester, MA from ฿2,082

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21 Oct - 22 Oct
Tomorrow
22 Oct - 23 Oct
This weekend
24 Oct - 26 Oct
Next weekend
31 Oct - 2 Nov

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Top 10 Chester hotels and places to stay

Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
9.0 out of 10, Wonderful, (1012)
"Great Indian restaurant in the hotel!"
United States
Chris
The price is ฿3,461
฿3,866 total
includes taxes & fees
3 Nov - 4 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Interior
Berkshires Untold
Berkshires Untold
3.5 star property
9.0 out of 10, Wonderful, (771)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is ฿2,874
฿3,210 total
includes taxes & fees
2 Nov - 3 Nov
Berkshires Untold
Exterior
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1015)
"Good breakfast King rooms are the best facing the mountains Recently remodeled "
United States
Susan M
The price is ฿4,159
฿4,646 total
includes taxes & fees
2 Nov - 3 Nov
The Yankee, Trademark Collection by Wyndham
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
8.0 out of 10, Very good, (915)
"Enjoyable stay. Staff were very nice. "
United States
Claire
The price is ฿3,355
฿3,748 total
includes taxes & fees
10 Nov - 11 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Front of property
The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires
3.5 star property
9.0 out of 10, Wonderful, (1010)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is ฿4,159
฿5,919 total
includes taxes & fees
26 Oct - 27 Oct
The Cornell Inn, Lenox & The Berkshires
Basic Studio, 1 King Bed | Desk, laptop workspace, free WiFi, bed sheets
River Valley Inn
River Valley Inn
2.0 star property
8.6 out of 10, Excellent, (82)
"Great quiet motel. "
United States
Hector
The price is ฿3,876
฿4,330 total
includes taxes & fees
9 Nov - 10 Nov
River Valley Inn
Lobby
Red Roof Inn PLUS+ West Springfield
Red Roof Inn PLUS+ West Springfield
2.5 star property
7.0 out of 10, Good, (1020)
"The staff was very helpful and nice"
United States
Cristal
The price is ฿3,195
฿3,657 total
includes taxes & fees
2 Nov - 3 Nov
Red Roof Inn PLUS+ West Springfield
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
9.4 out of 10, Exceptional, (55)
"Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout"
United States
Marti
The price is ฿4,679
฿5,227 total
includes taxes & fees
4 Nov - 5 Nov
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Front of property – evening/night
Hotel On North
Hotel On North
3.5 star property
9.6 out of 10, Exceptional, (783)
"Nice hotel. Very friendly and professional staff. "
United States
Magen
The price is ฿3,528
฿3,941 total
includes taxes & fees
5 Nov - 6 Nov
Hotel On North
In-room safe, desk, free cots/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
7.6 out of 10, Good, (554)
"Excellent location, friendly service, clean, comfortable room."
United States
Beth
The price is ฿2,443
฿2,729 total
includes taxes & fees
22 Oct - 23 Oct
Travelodge by Wyndham Great Barrington Berkshires
Outdoor pool, pool loungers
The Red Lion Inn
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (1014)
"Picture perfect Inn"
United States
jeff
The price is ฿4,854
฿6,877 total
includes taxes & fees
6 Nov - 7 Nov
The Red Lion Inn
Exterior
Candlewood Suites West Springfield by IHG
Candlewood Suites West Springfield by IHG
2.5 star property
8.4 out of 10, Very good, (772)
"Nice, friendly staff, clean room and comfortable suite.. highly recommend "
United States
Christopher
The price is ฿3,192
฿3,654 total
includes taxes & fees
26 Oct - 27 Oct
Candlewood Suites West Springfield by IHG
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
9.0 out of 10, Wonderful, (762)
"Lovely spot, great accommodations, friendly staff, and great location."
United States
Joanne
The price is ฿3,782
฿4,679 total
includes taxes & fees
3 Nov - 4 Nov
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8.8 out of 10, Excellent, (678)
"This motel was easy access right off the highway, super clean, and the staff was great. We would definitely stay here again. Breakfast options were good as well. "
United States
Tina
The price is ฿3,323
฿3,711 total
includes taxes & fees
16 Nov - 17 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3.0 star property
9.0 out of 10, Wonderful, (721)
"Great stay, perfect "
United States
Lawrence
The price is ฿3,036
฿4,119 total
includes taxes & fees
4 Nov - 5 Nov
Berkshire Mountain Lodge
Indoor pool
La Quinta Inn & Suites by Wyndham Springfield MA
La Quinta Inn & Suites by Wyndham Springfield MA
3.0 star property
8.2 out of 10, Very good, (1306)
"Love this hotel, 2nd time staying here, family friendly, clean, nice room, great restaurants, convenient location"
United States
Lynne
The price is ฿3,738
฿4,241 total
includes taxes & fees
10 Nov - 11 Nov
La Quinta Inn & Suites by Wyndham Springfield MA
Front of property
The Constance by the Lenox Collection
The Constance by the Lenox Collection
3.5 star property
8.4 out of 10, Very good, (554)
"Very quiet and comfortable "
United States
Beth
The price is ฿3,883
฿4,337 total
includes taxes & fees
18 Nov - 19 Nov
The Constance by the Lenox Collection
Check-in/check-out kiosk
Quality Inn West Springfield
Quality Inn West Springfield
2.5 star property
7.0 out of 10, Good, (1022)
"Convenient nice cozy hotel with breakfast included and spacious rooms. "
United States
Danielle
The price is ฿2,935
฿3,359 total
includes taxes & fees
16 Nov - 17 Nov
Quality Inn West Springfield
Standard Room, 1 King Bed | Desk, iron/ironing board, free cots/infant beds, rollaway beds
Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington
2.0 star property
6.4 out of 10, (640)
"Stayed one night just because we had been driving for 10 hours but nice place for the price. "
United States
patricia
The price is ฿1,864
฿2,082 total
includes taxes & fees
3 Nov - 4 Nov
Econo Lodge Lee - Great Barrington
Lobby
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
9.4 out of 10, Exceptional, (745)
"The property is very nice and the staff was extremely friendly and helpful."
United States
Greg
The price is ฿4,658
฿5,203 total
includes taxes & fees
3 Nov - 4 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.
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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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"In a very nice annex suite."
Julia 2-night trip
Posted 2 days ago
The Red Lion Inn

More cheap stays in Chester

Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield

1254 Riverdale Street, West Springfield, MA
The price is ฿3,195 per night from 2 Nov to 3 Nov
฿3,195
฿3,657 total
2 Nov - 3 Nov
includes taxes & fees
6.8/10 (1,014 reviews)

Frequently asked questions

What's the best place to stay in Chester?
La Quinta Inn & Suites by Wyndham Springfield MA, located 22.9 mi (36.8 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 Red Roof Inn PLUS+ West Springfield and Berkshire Mountain Lodge. 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.

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