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7 Jan - 8 Jan
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8 Jan - 9 Jan
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9 Jan - 11 Jan
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16 Jan - 18 Jan

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Our top choices for Chester hotels

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1002)
Located near Pittsfield train station, this hotel offers free breakfast, WiFi, and parking. Stay active in the fitness centre or enjoy nearby skiing options. Tanglewood Music Centre and Tracy Brook Wildlife Sanctuary await just minutes away, with clean rooms and helpful staff to welcome you.
"Very friendly and good Breakfast."
United States
Jesse
The price is NZ$148
includes taxes & fees
25 Jan - 26 Jan
Best Western Plus Berkshire Hills Inn & Suites
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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, (716)
Experience comfort in Great Barrington at this welcoming hotel with clean rooms and attentive service. Visit nearby Lake Mansfield Park or explore the Housatonic River after enjoying the indoor pool, fitness centre, and complimentary WiFi.
"Nice warm pool and hot tub. Good little fitness center. "
United States
Fawn
The price is NZ$189
includes taxes & fees
25 Jan - 26 Jan
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Lobby
Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield
2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1001)
Splash in the indoor pool or unwind at the bar after exploring nearby MGM Springfield and Basketball Hall of Fame. This Chicopee hotel offers free breakfast, WiFi, parking, and 24-hour fitness centre, with restaurants and shopping just steps away.
"Everything was perfect: clean room, great breakfast, courteous staff!"
United States
Tiffany
The price is NZ$175
includes taxes & fees
19 Jan - 20 Jan
Tru by Hilton Chicopee Springfield
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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, (1001)
Conveniently located a 6-minute walk from Pittsfield Intermodal Transport Centre, this hotel offers peaceful accommodation with an indoor pool. Enjoy the fitness centre, bar, and coffee shop after exploring nearby Berkshire Museum and Colonial Theatre.
"Everyone that works here is so nice! I’ve stayed here twice and had such a nice time. Thank youN"
United States
Melissa
The price is NZ$189
includes taxes & fees
9 Jan - 10 Jan
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Indoor pool
D. Hotel Suites & Spa

D. Hotel Suites & Spa

D. Hotel Suites & Spa
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (2262)
Adjacent to a golf course, this Holyoke spa hotel offers deep-tissue massages and body wraps. Enjoy American cuisine at The Mick restaurant, followed by drinks at the bar/lounge. The indoor pool and fitness centre complement the full-service spa experience.
"Great room and location."
United States
Karina
The price is NZ$234
includes taxes & fees
11 Jan - 12 Jan
D. Hotel Suites & Spa
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1011)
Immerse yourself in mountain vistas at this Lenox hotel, where peaceful accommodation include refrigerators and microwaves. Unwind in the spa pool, swim in the indoor or seasonal outdoor pool, and enjoy complimentary breakfast before exploring nearby attractions.
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is NZ$195
includes taxes & fees
15 Jan - 16 Jan
The Yankee, Trademark Collection by Wyndham
Miscellaneous
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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, (1001)
Enjoy panoramic lake vistas at this peaceful Lenox hotel, just 10 minutes from Tanglewood Music Centre. After working out in the 24-hour fitness centre, savour Indian cuisine at Mint restaurant while watching spectacular sunsets over the water.
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is NZ$189
includes taxes & fees
28 Jan - 29 Jan
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lobby
Blue – A Modern Hotel, an Ascend Collection Hotel

Blue – A Modern Hotel, an Ascend Collection Hotel

Blue – A Modern Hotel, an Ascend Collection Hotel
2.5 star property
West Springfield
9.6 out of 10, Exceptional, (116)
Explore attractions like Big E and MGM Springfield from this West Springfield hotel with free WiFi and parking. Enjoy hiking trails nearby or work out in the 24-hour fitness centre after visiting the Basketball Hall of Fame.
"New and still working some kinks out but overall a great stay. "
United States
Jesse
The price is NZ$218
includes taxes & fees
30 Jan - 31 Jan
Blue – A Modern Hotel, an Ascend Collection Hotel
View from property
Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke
2.5 star property
Holyoke
9.2 out of 10, Wonderful, (602)
Located just minutes from popular attractions, this hotel offers a refreshing indoor pool and fitness centre. Each room includes convenient refrigerators and microwaves, while free breakfast, WiFi and parking enhance your value. Guests consistently praise the helpful staff.
"Room was very clean, the breakfast was delicious!"
United States
William
The price is NZ$228
includes taxes & fees
25 Jan - 26 Jan
Fairfield Inn & Suites Springfield Holyoke
Front of property
The Ellery

The Ellery

The Ellery
3.5 star property
Northampton
9.2 out of 10, Wonderful, (936)
Steeped in New England charm, this cosy hotel offers free parking and Wi-Fi near the train station. Guests love the comfortable beds and friendly staff. Explore nearby Smith College Botanic Garden after enjoying the daily continental breakfast.
"Clean, lovely staff and breakfast "
United Kingdom
MICHAEL
The price is NZ$238
includes taxes & fees
21 Jan - 22 Jan
The Ellery
Exterior
Candlewood Suites West Springfield by IHG

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, (823)
Convenient Springfield location just minutes from attractions like Naismith Basketball Hall of Fame. Unwind in the spa pool after workouts, grab a snack at the café, and appreciate rooms with microwaves and refrigerators. Clean accommodation and helpful staff enhance the experience.
"The room was clean and staff was friendly. "
United States
Brian
The price is NZ$166
includes taxes & fees
1 Feb - 2 Feb
Candlewood Suites West Springfield by IHG
In-room safe, desk, free cots/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (566)
"Excellent location!!"
United States
Abdul Samad
The price is NZ$145
includes taxes & fees
11 Jan - 12 Jan
Travelodge by Wyndham Great Barrington Berkshires
Lobby
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1004)
Experience tranquility at this welcoming hotel, just 15 minutes from Tanglewood Music Centre. Guests praise the quiet atmosphere, helpful staff, and complimentary continental breakfast. Conveniently located near Lee Library and local restaurants with easy access to shopping.
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is NZ$159
includes taxes & fees
1 Feb - 2 Feb
Quality Inn Lee - Lenox South
Lobby
Hampton Inn Westfield

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very good, (821)
Located in Westfield, this hotel offers a complimentary breakfast that guests rave about. Take a refreshing dip in the indoor pool, work out in the fitness centre, or visit nearby General Wareham Park. Free WiFi and parking add convenience.
"I will stay again"
United States
Jailene
The price is NZ$221
includes taxes & fees
14 Jan - 15 Jan
Hampton Inn Westfield
Room, 2 Queen Beds, Non Smoking
Monument Mountain Motel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (814)
"Room was very well designed and clean. The woman who worked at the desk was wonderful!"
United States
Cynthia
Monument Mountain Motel
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

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, (818)
Nestled in the Berkshires, this family-friendly resort features 2 outdoor and 2 indoor swimming pools. Enjoy refreshments at the pool bar or coffee shop while staying near cultural attractions like Tanglewood Music Centre and Berkshire Theatre Festival.
"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
United States
Stephanie
The price is NZ$215
includes taxes & fees
15 Jan - 16 Jan
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
In-room safe, desk, laptop workspace, iron/ironing board
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (828)
This centrally located motel has an inviting outdoor pool where you can cool off after exploring nearby attractions. Free WiFi and self parking add extra value while the helpful staff ensures a pleasant stay in clean, comfortable rooms.
"Staff was very friendly and helpful."
United States
Pamela
The price is NZ$153
includes taxes & fees
9 Jan - 10 Jan
Howard Johnson by Wyndham Lenox
Lobby
Hampton Inn West Springfield

Hampton Inn West Springfield

Hampton Inn West Springfield
2.5 star property
West Springfield
8.2 out of 10, Very good, (1000)
This West Springfield hotel offers a tranquil atmosphere despite its central location. Enjoy the fitness centre and seasonal pool while staying minutes from MGM Springfield and Riverdale Shops. Guests consistently praise the helpful staff and immaculate accommodation.
"Very good place to stay"
United States
Gloria
The price is NZ$209
includes taxes & fees
11 Jan - 12 Jan
Hampton Inn West Springfield
Exterior
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

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, (761)
Tranquil accommodation in Great Barrington offer soundproof rooms for undisturbed sleep. The helpful staff, complimentary breakfast, and free parking enhance your stay, while restaurants within walking distance and nearby Housatonic River provide convenient exploration options.
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
The price is NZ$261
includes taxes & fees
22 Jan - 23 Jan
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Exterior
Best Western Springfield West Inn

Best Western Springfield West Inn

Best Western Springfield West Inn
2.5 star property
West Springfield
7.8 out of 10, Good, (1000)
Unwind in this quiet retreat featuring free WiFi, parking, and daily continental breakfast. Just 15 minutes from Six Flags New England and MGM Springfield, guests love the helpful staff and convenient location for business or leisure travel.
"Decent breakfast"
United States
Jennifer
The price is NZ$185
includes taxes & fees
14 Jan - 15 Jan
Best Western Springfield West 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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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 riverfront 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
"The staff was super helpful and courteous. The room and public areas were superb. We did not use the pool but the area was neatly kept and very attractive (brightly colored and well lit). The hotel is located in a safe area, surrounded by woods, and overlooking the Connecticut River."
Gary 1-night trip
Posted 2 days ago
D. Hotel Suites & Spa

More cheap accommodation in Chester

Riverdale Inn

Riverdale Inn

1500 Riverdale Street West Springfield MA
The price is NZ$136 per night from 11 Jan to 12 Jan
NZ$136
11 Jan - 12 Jan
includes taxes & fees
5.8/10 (1,001 reviews)

Frequently asked questions

What's the best place to stay in Chester?
D. Hotel Suites & Spa, located 19.1 mi (30.7 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 The Red Lion Inn and Holiday Inn & Suites Pittsfield-Berkshires by IHG. See all available top hotels, or vacation rentals in Chester.
What are some of the best holiday rentals that Chester has to offer?
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: This holiday home rental outside of Chester offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub. 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 Pyramid Lake and Blandford Ski Area 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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