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Chester Hotels

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Check Chester hotel prices

Tonight
Nov 15 - Nov 16
Tomorrow night
Nov 16 - Nov 17
This weekend
Nov 15 - Nov 17

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Top 10 trending Chester hotels

The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior
The Black Swan Lee - Lenox, Ascend Hotel Collection
3.0 star property
9.0 out of 10, Wonderful, (1004)
"We booked this place for a one-night stay to check out the Berkshires. This was pretty much centrally located from everything we wanted to visit. We chose this place for the country feel rather than the big city type hotels. The place was a little outdated but had the more of a home feel. There is some updating due there, but it wasn't a disappointment. We will book again when we visit the area to go hiking. Plus, the lake view was ok, and the water looked very clean. I will say this is an...
The price is P6,067
P6,776 total
includes taxes & fees
Dec 1 - Dec 2
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Red Lion Inn
Outdoor pool, sun loungers
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (1000)
"Excellent "
The price is P8,171
P11,753 total
includes taxes & fees
Nov 25 - Nov 26
The Red Lion Inn
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
3.5 star property
9.0 out of 10, Wonderful, (564)
"We had a one bedroom, and were surprised by how much room there was. Full kitchen, and a half bath downstairs. Close to a lot of the Berkshire's best attraction."
The price is P7,583
P9,127 total
includes taxes & fees
Dec 10 - Dec 11
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
The Constance, The Whitlock, & The Dewey By The Lenox Collection
Free WiFi, bed sheets
The Constance, The Whitlock, & The Dewey By The Lenox Collection
3.5 star property
8.6 out of 10, Excellent, (399)
"Lots of character, part of the center of town. Walk to downtown restaurants and shopping. "
The price is P5,596
P6,251 total
includes taxes & fees
Nov 17 - Nov 18
The Constance, The Whitlock, & The Dewey By The Lenox Collection
The Cornell Inn, Lenox
Porch
The Cornell Inn, Lenox
3.0 star property
8.8 out of 10, Excellent, (1001)
"Perfect romantic spot for a weekend getaway. Close enough to walk into town but far enough from crowds "
The price is P7,172
P8,411 total
includes taxes & fees
Nov 17 - Nov 18
The Cornell Inn, Lenox
The Little Lion
Exterior
The Little Lion
3.0 star property
8.8 out of 10, Excellent, (433)
"Their was a large bunch of hair caught under the bathroom door - I had to remove it myself- yuck"
The price is P4,359
P4,870 total
includes taxes & fees
Dec 1 - Dec 2
The Little Lion
Quality Inn
1 bedroom, premium bedding, pillowtop beds, desk
Quality Inn
2.5 star property
8.2 out of 10, Very Good, (1002)
"Decent room at a decent price. Only put off by musty smell in room. "
The price is P4,182
P4,672 total
includes taxes & fees
Dec 4 - Dec 5
Quality Inn
Lakehouse Inn
Aerial view
Lakehouse Inn
4.0 star property
9.8 out of 10, Exceptional, (228)
"Excellent place and location in the Berkshires."
The price is P8,759
P10,273 total
includes taxes & fees
Nov 23 - Nov 24
Lakehouse Inn
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Reception
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
9.2 out of 10, Wonderful, (671)
"Great hotel with nice staff and facilities. Close to grocery, restaurants and Stockbridge tourist attractions."
The price is P8,935
P9,981 total
includes taxes & fees
Nov 18 - Nov 19
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Premium bedding, pillowtop beds, in-room safe, desk
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
2.5 star property
8.8 out of 10, Excellent, (562)
"We came to the beautiful Berkshires to visit our daughter and family. We had a lovely comfortable stay for 2 nights where the staff was accommodating and friendly; bed was comfortable and room was spotlessly clean. The breakfast was wonderful. "
The price is P6,932
P7,743 total
includes taxes & fees
Dec 4 - Dec 5
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Blackberry River Inn
Library
Blackberry River Inn
3.0 star property
9.6 out of 10, Exceptional, (89)
"Have stayed here before and each time had a wonderful experience. The staff was also extremely helpful and the accommodations were impeccable. The breakfasts were delicious. We would definitely stay here again."
The price is P10,129
P11,648 total
includes taxes & fees
Nov 20 - Nov 21
Blackberry River Inn
Chambery Inn
Front of property
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (359)
"Lovely, unique property with huge rooms! Such a fun place to stay. "
The price is P11,160
P12,466 total
includes taxes & fees
Nov 24 - Nov 25
Chambery Inn
Monument Mountain Motel
Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
Monument Mountain Motel
2.5 star property
8.8 out of 10, Excellent, (677)
"Monument Mountain is a great bargain for a no-frills roadside motel. "
The price is P3,906
P4,363 total
includes taxes & fees
Nov 20 - Nov 21
Monument Mountain Motel
Little Cat Lodge
Seasonal outdoor pool
Little Cat Lodge
2.0 star property
9.0 out of 10, Wonderful, (27)
"Loved the place just go! "
The price is P11,631
P12,561 total
includes taxes & fees
Dec 1 - Dec 2
Little Cat Lodge
Quality Inn
Lobby
Quality Inn
2.5 star property
8.2 out of 10, Very Good, (1000)
"Very clean and comfortable. Would stay again!"
The price is P4,581
P5,116 total
includes taxes & fees
Dec 1 - Dec 2
Quality Inn
Whistler's Inn Bed & Breakfast
Property grounds
Whistler's Inn Bed & Breakfast
3.5 star property
7.8 out of 10, Good, (471)
"This bed and breakfast is a true gem, set in a beautifully preserved 1836 mansion. The rooms feature herringbone wood floors, diamond-pane windows, and soaring 11-inch ceilings, creating an atmosphere that feels both magical and timeless. With its charming, historic details and exceptionally friendly owners, staying here is like stepping into an enchanting, old-world retreat."
The price is P8,142
P10,211 total
includes taxes & fees
Nov 18 - Nov 19
Whistler's Inn Bed & Breakfast
Locust Tree Bed and Breakfast LLC
Terrace/patio
Locust Tree Bed and Breakfast LLC
3.0 star property
9.0 out of 10, Wonderful, (366)
"Nice room at reasonable price with breakfast included. "
The price is P6,168
P7,093 total
includes taxes & fees
Nov 26 - Nov 27
Locust Tree Bed and Breakfast LLC
Econo Lodge Lee - Great Barrington
Desk, iron/ironing board, free cribs/infant beds, rollaway beds
Econo Lodge Lee - Great Barrington
2.0 star property
6.2 out of 10, (578)
"We were looking for a place not too expensive to just spend the night. This place fit the bill; clean and comfy. Bathroom needed some work and the floors were quite slippery, just coming in from the bad weather. Nothing a few scatter rugs and bathmat could fix. Bed was comfortable and a nice little dining table for 2 near the window. We'd stay there again."
The price is P3,818
P4,265 total
includes taxes & fees
Nov 17 - Nov 18
Econo Lodge Lee - Great Barrington
Brook Farm Inn
Front of property
Brook Farm Inn
3.5 star property
9.4 out of 10, Exceptional, (147)
"Very charming inn. The staff was very friendly and helpful."
The price is P10,045
P11,220 total
includes taxes & fees
Nov 17 - Nov 18
Brook Farm Inn
East Rock Inn
Exterior
East Rock Inn
2.0 star property
9.2 out of 10, Wonderful, (11)
"Love this motel. Visit the area monthly, this was my 5th visit at East Rock, every time has been perfect."
The price is P6,788
P7,582 total
includes taxes & fees
Dec 17 - Dec 18
East Rock Inn
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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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 D. Hotel Suites & Spa 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! 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 are some hotels with pools in Chester?

La Quinta Inn & Suites by Wyndham Springfield MA: 3-star hotel located near Springfield Museums. Offers a children's pool, an indoor pool, and a snack bar. Tru by Hilton Chicopee Springfield and D. Hotel Suites & Spa are two additional hotels that feature an onsite pool. View all hotels with pools in Chester.

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 Becket Land Trust Historic Quarry 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.