Photo by Elizabeth Massa Peroulakis

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Top hotels and accommodation in Chester

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, (1003)
"Great Indian restaurant in the hotel!"
The price is NZ$204
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, (743)
"Great location and very clean. Beautifully decorated and the restaurant is amazing. Just wish it offered a free breakfast with the room. "
The price is NZ$168
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, (1001)
"Nice area to visit "
The price is NZ$247
includes taxes & fees
5 Oct - 6 Oct
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, (1003)
"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 Bathrooms a bit outdated, but great stay for the price."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 NZ$193
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, (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 NZ$312
includes taxes & fees
28 Oct - 29 Oct
The Cornell Inn, Lenox & The Berkshires
River Valley Inn
Basic Studio, 1 King Bed

River Valley Inn

2.0 star property
8.6 out of 10, Excellent, (70)
"Great quiet motel. "
The price is NZ$247
includes taxes & fees
5 Oct - 6 Oct
River Valley Inn
The Red Lion Inn
Outdoor pool, pool loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1003)
"great place have stayed several times, and hope to return."
The price is NZ$384
includes taxes & fees
4 Nov - 5 Nov
The Red Lion Inn
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, (745)
"The lodging was convenient to all the area attractions."
The price is NZ$246
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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, (887)
"Excellent customer service and great rooms"
The price is NZ$197
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn & Suites Pittsfield-Berkshires 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, (1276)
"Affordable and easy access to the Big E. Friendly staff. "
The price is NZ$232
includes taxes & fees
13 Oct - 14 Oct
La Quinta Inn & Suites by Wyndham Springfield MA
Candlewood Suites West Springfield by IHG
Exterior

Candlewood Suites West Springfield by IHG

2.5 star property
8.4 out of 10, Very good, (767)
"I would definitely stay here again!"
The price is NZ$192
includes taxes & fees
26 Oct - 27 Oct
Candlewood Suites West Springfield by IHG
The Constance by the Lenox Collection
Front of property

The Constance by the Lenox Collection

3.5 star property
8.4 out of 10, Very good, (548)
"Staff was so friendly and helpful. The room was small and comfortable and the grounds were well kept. "
The price is NZ$198
includes taxes & fees
3 Nov - 4 Nov
The Constance by the Lenox Collection
Hotel On North
Front of property – evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (777)
"Great property! Very large clean room in a unique hotel! "
The price is NZ$241
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, (671)
"Very convenient set up of both room and kitchen, resort very easy to navigate. "
The price is NZ$217
includes taxes & fees
2 Nov - 3 Nov
Berkshire Mountain Lodge
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
7.4 out of 10, Good, (550)
"Excellent location, friendly service, clean, comfortable room."
The price is NZ$144
includes taxes & fees
7 Oct - 8 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, (1001)
"Convenient nice cozy hotel with breakfast included and spacious rooms. "
The price is NZ$165
includes taxes & fees
19 Oct - 20 Oct
Quality Inn West Springfield
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, (49)
"Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout"
The price is NZ$275
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Fairfield Inn & Suites Springfield Northampton/Amherst
Lobby

Fairfield Inn & Suites Springfield Northampton/Amherst

3.0 star property
9.2 out of 10, Wonderful, (990)
"Clean room and convenient location "
The price is NZ$291
includes taxes & fees
2 Nov - 3 Nov
Fairfield Inn & Suites Springfield Northampton/Amherst
Econo Lodge Lee - Great Barrington
Standard Room, 1 King Bed

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (635)
"Easy check in"
The price is NZ$120
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, (2222)
"Best hotel option for the Easthampton area hands down. "
The price is NZ$219
includes taxes & fees
5 Oct - 6 Oct
D. Hotel Suites & Spa
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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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
"Great place! Food excellent ss well!"
Crystal 1-night trip
Posted 4 days ago
The Red Lion Inn

More cheap accommodation in Chester

More cheap accommodation in Chester

Quality Inn West Springfield

Quality Inn West Springfield

1150 Riverdale St, West Springfield, MA
The price is NZ$165 per night from 19 Oct to 20 Oct
NZ$165
19 Oct - 20 Oct
includes taxes & fees
7/10 Good! (1,036 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.

What are some of the best holiday rentals that Chester has to offer?

Spacious 5-bedroom house in charming Lee with WiFi: This holiday home rental outside of Chester offers a fireplace, a BBQ and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities such as a dishwasher and a microwave can make your holiday run smoothly. See all 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia