Photo by Elizabeth Massa Peroulakis

Chester Hotels

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15 Oct - 16 Oct
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16 Oct - 17 Oct
This weekend
17 Oct - 19 Oct
Next weekend
24 Oct - 26 Oct

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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, (1007)
"Great Indian restaurant in the hotel!"
The price is €102
includes taxes & fees
2 Nov - 3 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, (759)
"We had a nice room and the food was delicious. Great place to stay. "
The price is €84
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, (1009)
"Good breakfast King rooms are the best facing the mountains Recently remodeled "
The price is €129
includes taxes & fees
2 Nov - 3 Nov
The Yankee, Trademark Collection by Wyndham
Lobby
Red Roof Inn PLUS+ West Springfield
Red Roof Inn PLUS+ West Springfield
2.5 star property
7.0 out of 10, Good, (1013)
"The staff was very helpful and nice"
The price is €97
includes taxes & fees
2 Nov - 3 Nov
Red Roof Inn PLUS+ West Springfield
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, (901)
"Excellent customer service and great rooms"
The price is €99
includes taxes & fees
2 Nov - 3 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, (1006)
"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 "
The price is €157
includes taxes & fees
26 Oct - 27 Oct
The Cornell Inn, Lenox & The Berkshires
Basic Studio, 1 King Bed
River Valley Inn
River Valley Inn
2.0 star property
8.6 out of 10, Excellent, (77)
"Great quiet motel. "
The price is €115
includes taxes & fees
9 Nov - 10 Nov
River Valley Inn
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, (53)
"Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout"
The price is €115
includes taxes & fees
2 Nov - 3 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, (779)
"Great property! Very large clean room in a unique hotel! "
The price is €110
includes taxes & fees
11 Nov - 12 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, (552)
"Excellent location, friendly service, clean, comfortable room."
The price is €72
includes taxes & fees
19 Oct - 20 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, (1010)
"Picture perfect Inn"
The price is €182
includes taxes & fees
6 Nov - 7 Nov
The Red Lion Inn
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, (756)
"Lovely spot, great accommodations, friendly staff, and great location."
The price is €124
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Exterior
Candlewood Suites West Springfield by IHG
Candlewood Suites West Springfield by IHG
2.5 star property
8.4 out of 10, Very good, (771)
"Nice, friendly staff, clean room and comfortable suite.. highly recommend "
The price is €97
includes taxes & fees
13 Nov - 14 Nov
Candlewood Suites West Springfield by IHG
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3.0 star property
9.0 out of 10, Wonderful, (702)
"Great stay, perfect "
The price is €109
includes taxes & fees
2 Nov - 3 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, (1290)
"Affordable and easy access to the Big E. Friendly staff. "
The price is €112
includes taxes & fees
11 Nov - 12 Nov
La Quinta Inn & Suites by Wyndham Springfield MA
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, (675)
"Great place to have a girls night for old friends when one of us is back in town for a night. Very convenient place well kept. "
The price is €99
includes taxes & fees
10 Nov - 11 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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, (552)
"Very quiet and comfortable "
The price is €94
includes taxes & fees
3 Nov - 4 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, (1015)
"Convenient nice cozy hotel with breakfast included and spacious rooms. "
The price is €83
includes taxes & fees
29 Oct - 30 Oct
Quality Inn West Springfield
Standard Room, 1 King Bed
Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington
2.0 star property
6.4 out of 10, (638)
"Stayed one night just because we had been driving for 10 hours but nice place for the price. "
The price is €60
includes taxes & fees
2 Nov - 3 Nov
Econo Lodge Lee - Great Barrington
Lobby
Blue – A Modern Hotel, an Ascend Collection Hotel
Blue – A Modern Hotel, an Ascend Collection Hotel
2.5 star property
9.6 out of 10, Exceptional, (43)
"Nice hotel"
The price is €125
includes taxes & fees
29 Oct - 30 Oct
Blue – A Modern Hotel, an Ascend Collection Hotel
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
"Room was comfortable and clean. The Inn is beautiful. We went to the Lions Den both evenings and had a drink and listened to live music. We couldn’t get a table at the restaurant but there are other good options in walking distance. The only disappointment was that the fireplace in our room was not working. "
Beth 2-night trip
Posted 3 days ago
The Red Lion Inn

More cheap stays in Chester

Quality Inn West Springfield

Quality Inn West Springfield

1150 Riverdale St, West Springfield, MA
The price is €83 per night from 29 Oct to 30 Oct
€83
29 Oct - 30 Oct
includes taxes & fees
7/10 Good! (1,008 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.

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