Photo by Elizabeth Massa Peroulakis

Find hotels in Chester, MA from Rp1.395.272

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12 Nov - 13 Nov
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13 Nov - 14 Nov
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14 Nov - 16 Nov
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21 Nov - 23 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
Lee
9.0 out of 10, Wonderful, (1002)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is Rp1.826.111
Rp2.039.766 total
includes taxes & fees
12 Dec - 13 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Interior
Berkshires Untold

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (798)
"Easy parking, great community spaces, beautiful decor! "
United States
Kerry
The price is Rp1.542.927
Rp1.723.449 total
includes taxes & fees
23 Nov - 24 Nov
Berkshires Untold
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1002)
"Great place. Friendly staff and very well located. Great breakfast options. "
United States
Abiezer
The price is Rp1.678.723
Rp1.875.134 total
includes taxes & fees
7 Dec - 8 Dec
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
Pittsfield
8.0 out of 10, Very good, (952)
"Great stay! Nice quiet room for 2 little “alert “ to outside noise pups!! Comfy beds and central location for the day trips we had planned."
United States
Stacey
The price is Rp1.468.883
Rp1.640.752 total
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
Lenox
9.0 out of 10, Wonderful, (1002)
"Very friendly staff. "
United States
Pamela
The price is Rp2.145.035
Rp3.047.092 total
includes taxes & fees
23 Nov - 24 Nov
The Cornell Inn, Lenox & The Berkshires
Exterior
Candlewood Suites West Springfield by IHG

Candlewood Suites West Springfield by IHG

2.5 star property
West Springfield
8.4 out of 10, Very good, (783)
"staff was great! the borrow cabinet is an awesome feature and the pool and hot tub were amazing!"
United States
Kelly
The price is Rp1.632.092
Rp1.867.929 total
includes taxes & fees
16 Nov - 17 Nov
Candlewood Suites West Springfield by IHG
Basic Studio, 1 King Bed | Desk, laptop workspace, free WiFi, bed sheets
River Valley Inn

River Valley Inn

2.0 star property
West Hatfield
8.6 out of 10, Excellent, (93)
"Clean room, comfortable bed, nice shower! Owners were very nice - we will definitely stay here again!"
United States
Deb
The price is Rp1.981.826
Rp2.213.701 total
includes taxes & fees
16 Nov - 17 Nov
River Valley Inn
Outdoor pool, pool loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1002)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is Rp2.487.406
Rp3.524.320 total
includes taxes & fees
16 Nov - 17 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
South Lee
9.0 out of 10, Wonderful, (781)
"Place was great!"
United States
Benjamin
The price is Rp2.250.788
Rp2.746.620 total
includes taxes & fees
13 Nov - 14 Nov
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (753)
"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
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
Great Barrington
8.8 out of 10, Excellent, (692)
"Solid location, great room, good breakfast. Fair Price. Been 3 different times and look forward to returning again "
United States
Jamie
The price is Rp1.786.258
Rp1.995.250 total
includes taxes & fees
30 Nov - 1 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (58)
"Room was far from spotless but overall good and nice breakfast. "
United States
Hannah
The price is Rp1.967.670
Rp2.197.888 total
includes taxes & fees
7 Dec - 8 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
West Springfield
6.8 out of 10, (1000)
"Excellent "
United States
Laurence
The price is Rp1.408.928
Rp1.612.518 total
includes taxes & fees
11 Dec - 12 Dec
Red Roof Inn PLUS+ West Springfield
Front of property – evening/night
Hotel On North

Hotel On North

3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (796)
"Clean room and staff was super friendly"
United States
Yuen
The price is Rp2.221.465
Rp2.481.376 total
includes taxes & fees
19 Nov - 20 Nov
Hotel On North
Front of property
Chambery Inn

Chambery Inn

3.0 star property
Lee
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
Indoor pool
La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

3.0 star property
Metro Center
8.2 out of 10, Very good, (1296)
"This is our second stay and we cant wait to come back fod pur next trip!"
United States
Jordan
The price is Rp1.840.267
Rp2.087.782 total
includes taxes & fees
17 Nov - 18 Nov
La Quinta Inn & Suites by Wyndham Springfield MA
Check-in/check-out kiosk
Quality Inn West Springfield

Quality Inn West Springfield

2.5 star property
West Springfield
7.0 out of 10, Good, (1010)
"Room and staff were good "
United States
George
The price is Rp1.401.434
Rp1.603.941 total
includes taxes & fees
25 Nov - 26 Nov
Quality Inn West Springfield
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
Great Barrington
7.6 out of 10, Good, (558)
"I loved the stay people were nice loved the pool and internet was great "
United States
Jennifer
The price is Rp1.249.050
Rp1.395.272 total
includes taxes & fees
24 Nov - 25 Nov
Travelodge by Wyndham Great Barrington Berkshires
Lobby
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
Great Barrington
9.4 out of 10, Exceptional, (754)
"Clean room, very courteous staff "
United States
Thomas
The price is Rp2.381.522
Rp2.660.160 total
includes taxes & fees
24 Nov - 25 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Indoor pool
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3.0 star property
Holyoke
9.4 out of 10, Exceptional, (2250)
"Very clean room, great variety of food at breakfast, friendly and helpful staff."
United States
Liz
The price is Rp1.830.217
Rp2.126.123 total
includes taxes & fees
17 Nov - 18 Nov
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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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 forests 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

D. Hotel Suites & Spa

D. Hotel Suites & Spa

10/10 Excellent
"Very comfortable stay"
Connie 1-night trip
Posted 5 days ago
D. Hotel Suites & Spa

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 Rp1.408.928 per night from 11 Dec to 12 Dec
Rp1.408.928
Rp1.612.518 total
11 Dec - 12 Dec
includes taxes & fees
6.8/10 (1,001 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 Littleville Lake 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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