Photo by Elizabeth Massa Peroulakis

Search Chester hotels

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check Chester hotel prices

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

Filter by

Guest rating
Guest rating
Property class

Top hotels and accommodation in Chester

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 The place was a little outdated but had the more of a home feel.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 AU$178
includes taxes & fees
16 Dec - 17 Dec
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Red Lion Inn
Outdoor pool, pool loungers
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (1000)
"Excellent "
The price is AU$310
includes taxes & fees
25 Nov - 26 Nov
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 AU$240
includes taxes & fees
16 Dec - 17 Dec
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 AU$165
includes taxes & fees
17 Nov - 18 Nov
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 AU$221
includes taxes & fees
18 Nov - 19 Nov
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 AU$128
includes taxes & fees
17 Dec - 18 Dec
The Little Lion
Quality Inn
Standard Room, 2 Queen Beds, Non Smoking
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 AU$123
includes taxes & fees
16 Dec - 17 Dec
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 AU$271
includes taxes & fees
23 Nov - 24 Nov
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 AU$263
includes taxes & fees
19 Nov - 20 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Standard Room
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 AU$204
includes taxes & fees
3 Dec - 4 Dec
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 AU$307
includes taxes & fees
18 Nov - 19 Nov
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 AU$329
includes taxes & fees
17 Nov - 18 Nov
Chambery Inn
Monument Mountain Motel
Room, 1 Queen Bed, Non Smoking
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 AU$115
includes taxes & fees
26 Nov - 27 Nov
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 AU$331
includes taxes & fees
17 Dec - 18 Dec
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 AU$135
includes taxes & fees
16 Dec - 17 Dec
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 AU$269
includes taxes & fees
18 Nov - 19 Nov
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 AU$187
includes taxes & fees
26 Nov - 27 Nov
Locust Tree Bed and Breakfast LLC
Econo Lodge Lee - Great Barrington
Standard Room, 1 King Bed
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 AU$112
includes taxes & fees
21 Nov - 22 Nov
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 AU$296
includes taxes & fees
17 Nov - 18 Nov
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 AU$207
includes taxes & fees
17 Dec - 18 Dec
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.
Don't see what you're looking for?
See all available properties in Chester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 D. Hotel Suites & Spa and Quality Inn West Springfield. See all available top hotels, or vacation rentals in Chester.

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

Berkshire Village Carriage House - Super Private!!: This holiday home rental outside of Chester is located in the mountains, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of books in this rental home to help you unwind. 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 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 offer an on-site pool. View all hotels with pools 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 Becket Land Trust Historic Quarry 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.