Photo by Chris Addams

Hotels in Chester

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Check prices for these dates

Tonight
Mar 1 - Mar 2
Tomorrow
Mar 2 - Mar 3
Next weekend
Mar 6 - Mar 8
In two weeks
Mar 13 - Mar 15

Where to stay in Chester?

Standard Room, 2 Queen Beds, Non Smoking | Pillowtop beds, desk, laptop workspace, blackout drapes
Baldwin Inn & Suites, SureStay Collection by Best Western
Baldwin Inn & Suites, SureStay Collection by Best Western
2.5 star property
West Springfield
7.8 out of 10, Good, (121 reviews)
Wake up to a complimentary continental breakfast at this West Springfield haven. Just a 10-minute drive from thrilling Six Flags New England and MGM Springfield attractions, with hiking trails nearby. Enjoy free WiFi and parking during your adventure-filled stay.
The price is CNY598
CNY685 total
includes taxes & fees
Mar 3 - Mar 4
Baldwin Inn & Suites, SureStay Collection by Best Western
Exterior
River Valley Inn
River Valley Inn
2.0 star property
West Hatfield
8.4 out of 10, Very Good, (115 reviews)
Discover West Hatfield from this welcoming motel with 24-hour reception and complimentary WiFi. Explore nearby Pioneer Valley Indoor Karting or Connecticut River Greenway State Park, then return to hassle-free accommodations with free parking.
The price is CNY679
CNY759 total
includes taxes & fees
Mar 2 - Mar 3
River Valley Inn
Desk, laptop workspace, blackout drapes, iron/ironing board
Pleasant Valley Motel West Stockbridge
Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 reviews)
Escape to the heart of the Berkshires in this well-maintained motel close to Tanglewood Music Center. Free WiFi and parking make exploring local attractions like Hoffman's Pottery and Charles H. Baldwin & Sons effortless. Clean rooms and daily housekeeping ensure a comfortable stay.
The price is CNY401
CNY440 total
includes taxes & fees
Mar 3 - Mar 4
Pleasant Valley Motel West Stockbridge
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk
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, (1,000 reviews)
Escape to this Pittsfield hotel near the train station, with Tanglewood Music Center nearby. After enjoying the complimentary breakfast, explore local skiing trails or workout in the fitness center. Clean rooms and attentive staff create a welcoming mountain getaway.
The price is CNY659
CNY736 total
includes taxes & fees
Mar 3 - Mar 4
Best Western Plus Berkshire Hills Inn & Suites
Lobby
Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,001 reviews)
This peaceful Lee hotel offers free daily continental breakfast near local restaurants and shopping. Just minutes from Lee Library and Animagic Museum, guests praise the helpful staff. Enjoy convenient access to cultural attractions during your Berkshires stay.
The price is CNY586
CNY654 total
includes taxes & fees
Mar 22 - Mar 23
Quality Inn Lee - Lenox South
Lobby lounge
Element Lenox Berkshires
Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (21 reviews)
Embrace mountain charm at this Lenox hotel with free breakfast and parking. Take a refreshing dip in the indoor pool before heading to nearby Tanglewood or Kennedy Park. Grab a drink at the bar after exploring the scenic Berkshires.
The price is CNY954
CNY1,065 total
includes taxes & fees
Mar 8 - Mar 9
Element Lenox Berkshires
Family House | Terrace/patio
Becket Motel
Becket Motel
2.5 star property
Becket
6.8 out of 10, (60 reviews)
Tucked away in Becket, this motel offers convenient perks like free WiFi, complimentary parking, and room service. Hiking enthusiasts can explore nearby trails and visit the historic Becket Land Trust Quarry for outdoor adventures.
The price is CNY652
CNY958 total
includes taxes & fees
Apr 1 - Apr 2
Becket Motel
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, (741 reviews)
Refresh in the indoor pool at this welcoming Great Barrington hotel. The fitness center adds value to each stay, while free breakfast fuels adventures to nearby Lake Mansfield Park and Housatonic River. Guests rave about the clean rooms and helpful staff.
The price is CNY734
CNY820 total
includes taxes & fees
Mar 5 - Mar 6
Holiday Inn Express Hotel & Suites Great Barrington by IHG
In-room safe, desk, laptop workspace, iron/ironing board
Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (834 reviews)
Dive into Berkshires charm at this centrally located Lenox motel, where you'll enjoy the refreshing outdoor pool and free parking. Near Guido's Marketplace and Bousquet Ski Area, with clean rooms and exceptionally helpful staff to enhance your stay.
The price is CNY473
CNY529 total
includes taxes & fees
Mar 2 - Mar 3
Howard Johnson by Wyndham Lenox
In-room safe, desk, free cribs/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, (573 reviews)
The price is CNY515
CNY575 total
includes taxes & fees
Mar 2 - Mar 3
Travelodge by Wyndham Great Barrington Berkshires
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
Monument Mountain Motel
Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (824 reviews)
Monument Mountain Motel
Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu
East Rock Inn
East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (38 reviews)
This cozy motel offers complimentary WiFi and parking, making outdoor adventures hassle-free. Explore the nearby Housatonic River and River Walk, or try kayaking and mountain biking. Garden views provide a serene backdrop for your Berkshires escape.
The price is CNY845
CNY944 total
includes taxes & fees
Apr 1 - Apr 2
East Rock Inn
Terrace/patio
D. Hotel Suites & Spa
D. Hotel Suites & Spa
3.0 star property
Holyoke
9.4 out of 10, Exceptional, (2,207 reviews)
Escape to this golf course adjacent hotel with 2 restaurants and a relaxing spa offering deep-tissue massages. The pool and fitness center enhance your stay, while Mount Tom State Reservation provides nearby adventure opportunities.
D. Hotel Suites & Spa
View from property
Fairfield Inn & Suites Springfield Holyoke
Fairfield Inn & Suites Springfield Holyoke
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (614 reviews)
Wake up to complimentary breakfast at this convenient Holyoke retreat near MGM Springfield and the Big E. After exploring nearby attractions, unwind in the indoor pool or fitness center. Rooms offer refrigerators and microwaves, plus free WiFi and parking.
The price is CNY810
CNY904 total
includes taxes & fees
Mar 16 - Mar 17
Fairfield Inn & Suites Springfield Holyoke
Seasonal outdoor pool
Sunset Inn
Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (411 reviews)
Nestled in Lee, this motel offers easy access to Tanglewood Music Center, along with free WiFi and parking. Cool off in the seasonal outdoor pool after exploring nearby trails, or venture to Lee Library and Animagic Museum of Animation.
The price is CNY652
CNY728 total
includes taxes & fees
Mar 2 - Mar 3
Sunset Inn
In-room dining
Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (658 reviews)
This Lee motel offers a playful mini golf course on-site and free continental breakfast to start your day. Located near Greenock Country Club and Lee Premium Outlets, guests praise the helpful staff. Enjoy complimentary WiFi and parking during your stay.
The price is CNY417
CNY466 total
includes taxes & fees
Apr 1 - Apr 2
Econo Lodge Lee - Great Barrington
Exterior
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
Discover this Lenox retreat with stunning mountain views, year-round swimming options, and fireplaces in select rooms. Just minutes from Bousquet Ski Area and local attractions, enjoy free breakfast and helpful staff after a day exploring.
The price is CNY636
CNY710 total
includes taxes & fees
Mar 8 - Mar 9
The Yankee, Trademark Collection by Wyndham
Indoor pool
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (84 reviews)
Escape to the heart of Pittsfield where this hotel offers an indoor pool and relaxing hot tub after exploring Tanglewood. Free breakfast, WiFi, and parking enhance your stay while nearby Guido's Marketplace awaits your discovery.
The price is CNY906
CNY1,012 total
includes taxes & fees
Mar 8 - Mar 9
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Lobby
Hampton Inn West Springfield
Hampton Inn West Springfield
2.5 star property
West Springfield
8.2 out of 10, Very Good, (1,000 reviews)
Escape the ordinary at this quiet haven with a seasonal outdoor pool and fitness center. Just a 15-minute drive to major attractions and close to Riverdale Shops. The helpful staff and clean rooms earn consistent praise from fellow travelers.
The price is CNY726
CNY831 total
includes taxes & fees
Mar 3 - Mar 4
Hampton Inn West Springfield
Lobby lounge
Berkshires Untold
Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (865 reviews)
Nestled in Lenox, this lodge offers easy access to Kennedy Park and Pleasant Valley Wilderness Sanctuary. The Club Room serves American cuisine, while the terrace provides a perfect spot to unwind after exploring local attractions.
The price is CNY687
CNY767 total
includes taxes & fees
Mar 2 - Mar 3
Berkshires Untold
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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Top landmarks in Chester

Chester Town Hall

If you’re after a show while in the center of Chester, you might want to get tickets at Chester Town Hall. If you want to experience more of the culture Chester has to offer, head to Becket Land Trust Historic Quarry, Littleville Lake, and Glendale Falls.
See properties

Learn more about Chester

The region around Chester is home to attractions such as Chester Town Hall and Littleville Lake.

See all hotels in Chester
An amazing keystone arch bridge!
Photo by Chris Addams
Open Photo by Chris Addams

Check out reviews of Chester hotels guests love

Residence Inn Springfield Chicopee

Residence Inn Springfield Chicopee

10/10 Excellent
"Clean room, friendly staff. "
Samkeliso 3-night trip
Posted 1 day ago
Residence Inn Springfield Chicopee

Frequently asked questions

How much does a hotel room cost in Chester?
You can choose a great hotel in Chester from CNY440 with properties to suit all budgets and needs. If you're looking for an affordable hotel in Chester that meets all of your requirements, just sort hotels by "Price: low to high" after applying your filters when searching on Hotels.com.
How can I find deals and earn rewards at Chester hotels?
Discover great deals on Chester hotel stays with Hotels.com. You can also look at hotel prices mid-week or during the low season to find off-peak deals. If you're up for a spontaneous trip, don't forget to check out our last-minute deals on Chester hotels.
Can I book Chester hotels with free cancellation?
In order to book a refundable Chester hotel, simply filter hotels by "Property cancellation options" and select "Fully refundable property". The majority of hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.
Can I book a refundable accommodation in Chester?
If you're looking for the flexibility to change your travel plans to Chester, most hotels offer refundable* bookable rates. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.
What will the weather in Chester be like during my vacation?
July and August are typically the warmest months in Chester when the average temp is 66°F. January and February are the coldest months when the average temperature is 28°F. July and August are the months with the most rain.
Why should I book my Chester hotel through Hotels.com?
There are lots of reasons to book your Chester trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.