Photo by Elizabeth Massa Peroulakis

Chester Hotels from S$99

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Tonight
6 Nov - 7 Nov
Tomorrow
7 Nov - 8 Nov
This weekend
7 Nov - 9 Nov
Next weekend
14 Nov - 16 Nov

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Top 10 trending Chester hotels

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, (1003)
"Good for one night stay"
United States
Marla
The price is S$160
includes taxes & fees
30 Nov - 1 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Interior
Berkshires Untold
Berkshires Untold
3.5 star property
9.0 out of 10, Wonderful, (791)
"Easy parking, great community spaces, beautiful decor! "
United States
Kerry
The price is S$135
includes taxes & fees
16 Nov - 17 Nov
Berkshires Untold
Exterior
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.2 out of 10, Wonderful, (1000)
"Great place. Friendly staff and very well located. Great breakfast options. "
United States
Abiezer
The price is S$148
includes taxes & fees
18 Nov - 19 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, (941)
"Enjoyable stay. Staff were very nice. "
United States
Claire
The price is S$143
includes taxes & fees
21 Nov - 22 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, (1000)
"Honestly I just enjoyed being able to relax Play some games in the cute pub and the breakfast was yummy and stuff was inviting and so helpful "
United States
Sandra
The price is S$239
includes taxes & fees
9 Nov - 10 Nov
The Cornell Inn, Lenox & The Berkshires
Desk, laptop workspace, free WiFi, bed sheets
River Valley Inn
River Valley Inn
2.0 star property
8.6 out of 10, Excellent, (90)
"Room was very clean. Owners are great Close to all things in Deerfield Would definitely stay there again "
United States
Kenneth
The price is S$173
includes taxes & fees
9 Nov - 10 Nov
River Valley 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, (780)
"staff was great! the borrow cabinet is an awesome feature and the pool and hot tub were amazing!"
United States
Kelly
The price is S$146
includes taxes & fees
30 Nov - 1 Dec
Candlewood Suites West Springfield by IHG
Outdoor pool, pool loungers
The Red Lion Inn
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (1001)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is S$264
includes taxes & fees
12 Nov - 13 Nov
The Red Lion Inn
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, (690)
"Solid location, great room, good breakfast. Fair Price. Been 3 different times and look forward to returning again "
United States
Jamie
The price is S$149
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, (747)
"Everything was so perfect for a weekend to just get away and decompress, the staff were great, the room was awesome. "
United States
Jeff
Berkshire Mountain Lodge
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, (56)
"Bright new hotel with very friendly and helpful staff. "
United States
Mary
The price is S$172
includes taxes & fees
2 Dec - 3 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Lobby
Red Roof Inn PLUS+ West Springfield
Red Roof Inn PLUS+ West Springfield
2.5 star property
6.8 out of 10, (1000)
"Excellent "
United States
Laurence
The price is S$126
includes taxes & fees
1 Dec - 2 Dec
Red Roof Inn PLUS+ West Springfield
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, (779)
"Place was great!"
United States
Benjamin
The price is S$184
includes taxes & fees
9 Nov - 10 Nov
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Front of property – evening/night
Hotel On North
Hotel On North
3.5 star property
9.6 out of 10, Exceptional, (792)
"Perfect Stay in the Berkshire This hotel was spacious, clean, and had everything needed for a comfortable stay. The room was well-maintained, and the location was ideal—close to local attractions and easy to get around. Smooth check-in process and great access throughout. Highly recommend! "
United States
Ann
The price is S$194
includes taxes & fees
16 Nov - 17 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, (556)
"I loved the stay people were nice loved the pool and internet was great "
United States
Jennifer
The price is S$109
includes taxes & fees
8 Nov - 9 Nov
Travelodge by Wyndham Great Barrington Berkshires
Check-in/check-out kiosk
Quality Inn West Springfield
Quality Inn West Springfield
2.5 star property
7.0 out of 10, Good, (1001)
"Convenient nice cozy hotel with breakfast included and spacious rooms. "
United States
Danielle
The price is S$133
includes taxes & fees
16 Nov - 17 Nov
Quality Inn West Springfield
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, (1290)
"This is our second stay and we cant wait to come back fod pur next trip!"
United States
Jordan
The price is S$163
includes taxes & fees
9 Nov - 10 Nov
La Quinta Inn & Suites by Wyndham Springfield MA
Front of property
Chambery Inn
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (372)
"We LOVED our mini getaway at the Chambery Inn. The room was gorgeous, spacious, and very comfortable. The fireplace couldn't have been easier to operate. The jetted tubs were divine with plenty of hot water the towel warmer was a nice bonus. The room was fully stocked with glassware and a corkscrew which was appreciated. We look forward to coming back"
United States
Samuel
Chambery Inn
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, (751)
"Very friendly and accommodating staff. Room was clean, which is very important to us. Breakfast in the morning was great. Nice variety of items and nice and fresh. It saved us money and the hassles of finding a breakfast restaurant. We are very pleased with our stay. "
United States
John
The price is S$208
includes taxes & fees
20 Nov - 21 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express
FairBridge Inn Express
2.5 star property
5.4 out of 10, (807)
"Room spotless and staff helpful."
United States
William
The price is S$99
includes taxes & fees
20 Nov - 21 Nov
FairBridge Inn Express
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
Frozen Sanderson Brook Falls in Chester
Photo by Elizabeth Massa Peroulakis
Open Photo by Elizabeth Massa Peroulakis

Top Chester Hotel Reviews

La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

10/10 Excellent
"Yes"
robert 1-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Springfield MA

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 S$126 per night from 1 Dec to 2 Dec
S$126
1 Dec - 2 Dec
includes taxes & fees
6.8/10 (1,006 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 Berkshire Mountain Lodge and Quality Inn West Springfield. 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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