Photo by Elizabeth Massa Peroulakis

Chester Hotels

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Top 10 trending Chester hotels

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 P6,149
P6,868 total
includes taxes & fees
Nov 2 - Nov 3
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 P5,064
P5,656 total
includes taxes & fees
Nov 2 - Nov 3
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 P7,760
P8,668 total
includes taxes & fees
Nov 2 - Nov 3
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, (1005)
"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 Bathrooms a bit outdated, but great stay for the price."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 P5,677
P6,497 total
includes taxes & fees
Nov 3 - Nov 4
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, (1003)
"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 P7,389
P10,516 total
includes taxes & fees
Oct 28 - Oct 29
The Cornell Inn, Lenox & The Berkshires
River Valley Inn
Desk, laptop workspace, free WiFi, bed sheets

River Valley Inn

2.0 star property
8.6 out of 10, Excellent, (70)
"Great quiet motel. "
The price is P7,465
P8,339 total
includes taxes & fees
Oct 6 - Oct 7
River Valley Inn
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1004)
"great place have stayed several times, and hope to return."
The price is P9,780
P13,510 total
includes taxes & fees
Nov 4 - Nov 5
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, (746)
"The lodging was convenient to all the area attractions."
The price is P6,719
P8,313 total
includes taxes & fees
Nov 2 - Nov 3
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, (889)
"Excellent customer service and great rooms"
The price is P5,961
P6,658 total
includes taxes & fees
Nov 2 - Nov 3
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 P6,887
P7,813 total
includes taxes & fees
Oct 13 - Oct 14
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, (768)
"I would definitely stay here again!"
The price is P5,671
P6,491 total
includes taxes & fees
Oct 26 - Oct 27
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 P5,970
P6,668 total
includes taxes & fees
Nov 3 - Nov 4
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 P7,292
P8,145 total
includes taxes & fees
Nov 3 - Nov 4
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 P5,394
P7,318 total
includes taxes & fees
Nov 2 - Nov 3
Berkshire Mountain Lodge
Travelodge by Wyndham Great Barrington Berkshires
In-room safe, desk, free cribs/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 P4,340
P4,848 total
includes taxes & fees
Oct 7 - Oct 8
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, (1002)
"Convenient nice cozy hotel with breakfast included and spacious rooms. "
The price is P4,870
P5,573 total
includes taxes & fees
Oct 19 - Oct 20
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 P8,313
P9,286 total
includes taxes & fees
Nov 2 - Nov 3
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 P8,796
P9,825 total
includes taxes & fees
Nov 2 - Nov 3
Fairfield Inn & Suites Springfield Northampton/Amherst
Econo Lodge Lee - Great Barrington
Desk, iron/ironing board, free cribs/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 P3,630
P4,055 total
includes taxes & fees
Nov 2 - Nov 3
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 P6,360
P7,388 total
includes taxes & fees
Oct 7 - Oct 8
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

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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
"The customer service employee was so nice and the room was clean . Also felt very safe and quiet "
katricia 1-night trip
Posted 19 hours ago
La Quinta Inn & Suites by Wyndham Springfield MA

More cheap stays in Chester

More cheap stays in Chester

Quality Inn West Springfield

Quality Inn West Springfield

1150 Riverdale St, West Springfield, MA
The price is P4,870 per night from Oct 19 to Oct 20
P4,870
P5,573 total
Oct 19 - Oct 20
includes taxes & fees
7/10 Good! (1,032 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 traveler data. Other good choices for your trip 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! Most hotel bookings are fully refundable as long as you cancel before the accommodation's cancellation deadline, which often is within 24-48 hours of your check-in date. If you have a non-refundable reservation, it may still be possible to cancel it and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Chester.

Where can I learn more about changing or cancelling my trip to Chester?

For additional details about picking new dates or cancelling your trip to Chester, go to https://www.expedia.com/service/.

What's the best accommodation near Logan International Airport (BOS)?

Hilton Boston Logan Airport is a popular 4-star hotel featuring a restaurant and an indoor pool. It's located a short 0.2 mi (0.4 km) from Logan Intl. Airport. Other accommodations close to the airport are Hyatt Regency Boston Harbor and Embassy Suites Boston Logan Airport.

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, theaters, and monuments. In Chester, there are 2 hotels and other accommodations to choose from. Find out more about Chester.

What should I see while I'm in Chester?

A favorite place to visit is Chester Town Hall. You'll also find Glendale Falls and Pyramid Lake in the area. Check out what more to see and do in Expedia's Chester guide.

What's the seasonal weather like in Chester?

The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Chester are January, February, November, and March, with each month seeing an average of 6 inches of snowfall.

Explore a world of travel with Expedia

Explore a world of travel with Expedia