Photo by Elizabeth Massa Peroulakis

Chester hotels from HK$614

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Our top choices for Chester hotels

In-room safe, individually decorated, individually furnished, desk
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, (1001)
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 HK$594
HK$663 total
includes taxes & fees
8 Jan - 9 Jan 2026
Best Western Plus Berkshire Hills Inn & Suites
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, (1002)
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 HK$695
HK$789 total
includes taxes & fees
1 Jan - 2 Jan 2026
Tru by Hilton Chicopee Springfield
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, (1000)
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 HK$780
HK$871 total
includes taxes & fees
14 Jan - 15 Jan 2026
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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, (1000)
Immerse yourself in mountain vistas at this Lenox hotel, where peaceful accommodation include refrigerators and microwaves. Unwind in the hot tub, 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 HK$721
HK$805 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Yankee, Trademark Collection by Wyndham
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, (997)
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.
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is HK$686
HK$766 total
includes taxes & fees
2 Jan - 3 Jan 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Lobby
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (14)
Located minutes from Tanglewood Music Centre, this Lenox hotel offers an indoor pool, bar, and free parking. Grab coffee at the café before exploring nearby Kennedy Park. Business travellers will appreciate the free WiFi and convenient amenities.
"Rooms were very clean and spacious."
United States
Morgan
The price is HK$1,050
HK$1,173 total
includes taxes & fees
8 Jan - 9 Jan 2026
Element Lenox 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, (1000)
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.
"The staff is always so helpful & nice, and the rooms are always clean and comfortable. This is my favorite place to stay in Lee!"
United States
Cooper
The price is HK$643
HK$718 total
includes taxes & fees
8 Jan - 9 Jan 2026
Quality Inn Lee - Lenox South
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, (710)
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.
"Great hospitality "
United States
regina maria
The price is HK$832
HK$929 total
includes taxes & fees
8 Jan - 9 Jan 2026
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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, (111)
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 HK$901
HK$1,032 total
includes taxes & fees
25 Jan - 26 Jan 2026
Blue – A Modern Hotel, an Ascend Collection Hotel
Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi
Monument Mountain Motel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (810)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
Monument Mountain Motel
Indoor pool
D. Hotel Suites & Spa

D. Hotel Suites & Spa

D. Hotel Suites & Spa
3.0 star property
Holyoke
9.4 out of 10, Exceptional, (2249)
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.
"The room was clean quiet and breakfast is great!! "
United States
Amanda
The price is HK$849
HK$987 total
includes taxes & fees
2 Jan - 3 Jan 2026
D. Hotel Suites & Spa
Front of property
The Ellery

The Ellery

The Ellery
3.5 star property
Northampton
9.2 out of 10, Wonderful, (928)
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 HK$957
HK$1,069 total
includes taxes & fees
8 Jan - 9 Jan 2026
The Ellery
Free daily buffet breakfast
Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (904)
Enjoy peaceful accommodation praised by travellers for their quiet atmosphere. This business-friendly hotel provides free breakfast, WiFi, and parking, with helpful staff ready to assist. Conveniently located near General Wareham Park and Gateway Entrance Park.
"We left too early for breakfast. Parking was fine "
United States
Virginia
The price is HK$727
HK$812 total
includes taxes & fees
11 Jan - 12 Jan 2026
Quality Inn Westfield - Springfield
Restaurant
Hampton Inn Hadley-Amherst Area

Hampton Inn Hadley-Amherst Area

Hampton Inn Hadley-Amherst Area
2.5 star property
Hadley
9.0 out of 10, Wonderful, (959)
Discover this Hadley hotel with an indoor pool for morning swims, just minutes from UMass Amherst. Guests love the helpful staff and clean rooms. Enjoy complimentary breakfast, WiFi, and parking while exploring nearby Hadley Farm Museum.
"Great welcome at front desk."
United States
RAYMAN
The price is HK$1,014
HK$1,132 total
includes taxes & fees
22 Jan - 23 Jan 2026
Hampton Inn Hadley-Amherst Area
Pillow-top beds, desk, laptop workspace, blackout curtains
Baldwin Inn & Suites, SureStay Collection by Best Western

Baldwin Inn & Suites, SureStay Collection by Best Western

Baldwin Inn & Suites, SureStay Collection by Best Western
2.5 star property
West Springfield
7.6 out of 10, Good, (105)
Unwind at this welcoming hotel featuring free breakfast, WiFi, and parking. Adventure awaits with nearby hiking trails, mountain biking, and just a 10-minute drive to Six Flags New England and MGM Springfield. Springfield Union Station is only 9 minutes away.
"At the moment breakfast isn’t being served but not a big deal, parking was very easy and close to the entrance not much walking having to be done, staff was very friendly and accommodating the place was very clean and very quiet definitely worth the money in my opinion looking forward to staying again "
United States
Victor
The price is HK$788
HK$902 total
includes taxes & fees
2 Jan - 3 Jan 2026
Baldwin Inn & Suites, SureStay Collection by Best Western
Exterior
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1002)
"Old time charm and hot tub under the stars"
United States
Lori
The price is HK$1,120
HK$1,599 total
includes taxes & fees
14 Jan - 15 Jan 2026
The Red Lion Inn
Lobby
Hampton Inn Westfield

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very good, (817)
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.
"Very pet friendly and the night check in agent was super kind and friendly"
United States
olivia townsend
The price is HK$899
HK$1,004 total
includes taxes & fees
11 Jan - 12 Jan 2026
Hampton Inn Westfield
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (659)
Explore Berkshire County from this Pittsfield hotel featuring an indoor pool and fitness centre. Enjoy meals at Jae's Asian Fusion restaurant and bar, plus in-room refrigerators and microwaves. Nearby attractions include Herman Melville's Arrowhead and Guido's Marketplace.
"The room was very clean with comfortable King bed. We really enjoyed the hot tub."
United States
Christine
The price is HK$994
HK$1,111 total
includes taxes & fees
9 Jan - 10 Jan 2026
Hilton Garden Inn Lenox Pittsfield
Desk, laptop workspace, blackout curtains, iron/ironing board
Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1001)
Surrounded by the beauty of West Stockbridge, this welcoming motel offers clean, comfortable rooms with complimentary WiFi and parking. Just 15 minutes from Tanglewood Music Centre and near local attractions like Hoffman's Pottery.
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is HK$404
HK$443 total
includes taxes & fees
4 Jan - 5 Jan 2026
Pleasant Valley Motel West Stockbridge
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 HK$614
HK$686 total
includes taxes & fees
8 Jan - 9 Jan 2026
Howard Johnson by Wyndham Lenox
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
Frozen Sanderson Brook Falls in Chester
Photo by Elizabeth Massa Peroulakis
Open Photo by Elizabeth Massa Peroulakis

Top Chester Hotel Reviews

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

10/10 Excellent
"Perfect for a weekend away. Stagg was friendly. Room was clean and spacious. It was everything we needed and more."
Cynthia 2-night trip
Posted 18 hours ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

More cheap stays in Chester

Riverdale Inn

Riverdale Inn

1500 Riverdale Street West Springfield MA
The price is HK$536 per night from 31 Dec to 1 Jan
HK$536
HK$614 total
31 Dec - 1 Jan 2026
includes taxes & fees
5.8/10 (999 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 La Quinta Inn & Suites by Wyndham Springfield MA and The Yankee, Trademark Collection by Wyndham. See all available top hotels, or vacation rentals in Chester.
What are some of the best holiday rentals that Chester has to offer?
Peace and quiet on the lake: This holiday home rental outside of Chester is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games 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 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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