Top 10 Hotels in Chester, MA from ￥12,327 - Competitive Prices

Our top choices for Chester hotels

Riverdale Inn

West Springfield

Jessica

￥13,992 total

includes taxes & fees

Jun 21 - Jun 22

Room, 2 Queen Beds, Refrigerator | Premium bedding, desk, laptop workspace, blackout drapes

Hampton Inn Westfield

Westfield

Lawrence

￥22,741 total

includes taxes & fees

Jun 30 - Jul 1

Fairfield Inn & Suites Springfield Holyoke

Holyoke

Joanne

￥23,413 total

includes taxes & fees

Jun 21 - Jun 22

D. Hotel Suites & Spa

Holyoke

Candyce

￥22,774 total

includes taxes & fees

Jun 8 - Jun 9

Candlewood Suites West Springfield by IHG

West Springfield

Lori

￥17,244 total

includes taxes & fees

Jun 14 - Jun 15

Best Western Springfield West Inn

West Springfield

Norbert

￥16,846 total

includes taxes & fees

Jun 14 - Jun 15

Red Roof Inn PLUS+ West Springfield

West Springfield

Donell

￥16,343 total

includes taxes & fees

Jun 9 - Jun 10

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk

Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Anandaraja

￥19,874 total

includes taxes & fees

Jun 9 - Jun 10

Quality Inn Westfield - Springfield

Westfield

Scott

￥17,768 total

includes taxes & fees

Jun 28 - Jun 29

Hampton Inn West Springfield

West Springfield

Sherry

￥19,405 total

includes taxes & fees

Jul 5 - Jul 6

Studio Suite, Multiple Beds | Bathroom | Hair dryer, towels, soap, shampoo

River Valley Inn

West Hatfield

Vidita

￥17,355 total

includes taxes & fees

Jun 30 - Jul 1

Standard Room, 2 Queen Beds, Non Smoking | Pillowtop beds, desk, laptop workspace, blackout drapes

Baldwin Inn & Suites, SureStay Collection by Best Western

West Springfield

Chris

￥17,435 total

includes taxes & fees

Jun 9 - Jun 10

Tru by Hilton Chicopee Springfield

Chicopee

Geovani

￥23,259 total

includes taxes & fees

Jul 2 - Jul 3

Residence Inn Springfield Chicopee

Chicopee

Rose

￥29,163 total

includes taxes & fees

Jun 14 - Jun 15

Hotel Northampton

Northampton

Shaena

￥26,540 total

includes taxes & fees

Jun 9 - Jun 10

Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

Pittsfield

William

￥12,327 total

includes taxes & fees

Jun 21 - Jun 22

The Ellery

Northampton

Judith

￥20,884 total

includes taxes & fees

Jun 29 - Jun 30

Room (Louis XIV) | Individually decorated, individually furnished, iron/ironing board

Naomi's Inn Bed & Breakfast

Liberty Heights

John

￥20,696 total

includes taxes & fees

Jun 7 - Jun 8

Superior Room, 1 King Bed, Jetted Tub | Jetted tub

The Yankee Inn

Lenox

Mark

￥39,962 total

includes taxes & fees

Jun 19 - Jun 20

Hampton Inn Chicopee/Springfield

Chicopee

Rosa

￥19,204 total

includes taxes & fees

Jun 21 - Jun 22

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Stay near popular Chester attractions

Chester Town Hall

You can get tickets for a performance at Chester Town Hall during your trip to Chester. Wander the lakeside and forest in this relaxing area.

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Learn more about Chester

Experience the hiking, camping, and waterfalls in Chester!

See all hotels in Chester

Top Chester Hotel Reviews

Quality Inn & Suites Northampton - Amherst

10/10 Excellent

"Room was very comfy but tub was not fillable except by the shower. There was no decaf coffee available. The person at the desk sait it was being made but it never showed up,"

Candlewood Suites West Springfield by IHG

2/10 Terrible

"I made a one night reservation and pre-paid my reservation/ Got to the hotel to check in and a very surly person proceeded to check me in. First telling me thati didn't pre-pay, and quoted me a price well more that i was charged on the expedia site. They insisted I did not prepay, once they found my reservation. I pulled up a copy of my itinerary showing paid in full and they said oh. okay, it's all set, and took a card for incidentals. Hotel and room are awkwardly decorated, that's the only way I can describe it. Electrical plugs are not conveniently placed- none at bedside, lamp wiring runs all over the floor to reach plugs; a recliner is right up against the side of the bed- no clearance. Bathroom has a huge scratched up wooden shelf holding a hand towel. Anyway, I confirmed the next morning that my long term lodging was all set, had coffee and purchased a cheese serving for breakfast, charged to my room. Checked out and went on my way. I received a receipt e-mailed later that day for another room charge in addition to the small breakfast. I notified the hotel immediately, and the only response from hotel and expedia was a copy of the hotel's charge to my credit card. I responded with a copy of my prepaid receipt, sent to me by expedia, and am waiting for a resolution or I will take it up with my credit card carrier."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Wonderful hidden gem of a little hotel. Right on lake laurel we had a beautiful lake view. Rooms were very clean. Decent breakfast. Well Located and close to Lee downtown main st, the Lennox Main Street and Stockbridge as well. Looking forward to returning"

Berkshires Untold

8/10 Good

"Here’s what we liked: If we were just reviewing BERKSHIRES UNTOLD based on the staff, we’d be giving it a 5. The staff were extremely friendly, helpful and gracious. When we asked for extra towels and requested a room change, they accommodated those requests immediately. After we switched rooms they checked to see if we were happier. This is exactly the kind of service you want in a hotel or inn. Other good things - The bed was comfortable and there was enough counter space in the bathroom and at the desk area. We also liked that there was a breakfast seating area, bar and small indoor seating area plus outdoor seating with gas fire pits. So, why are we giving the place a 3 overall? It really needed more attention to detail. The carpet in our original room was not in good shape and the fitted bed sheet had a small rip on my side. Some of the room furniture was dinged up and a sofa in the common seating area had some shredded fabric. One thing we didn’t like (that they couldn’t exactly help) was that we were there on a late spring wedding weekend, so there were buses idling in front of our room with loud talkers and smokers nearby. It felt like they were in our room along with the smoke and fumes. The trend of turning motels into better motels is interesting. They’re less expensive and are sometimes more original. But you’re still in a motel. If you value soundproofing and consistently better quality, a mid range chain may be a better choice."

Berkshire Mountain Lodge

10/10 Excellent

"We love the Bershire Mountain Lodge. We've stayed here five other times but this time we do have a few very minor negatives. 1) The cabinet door under the kitchenette sink had a loose hinge. We messaged the staff and requested that they wait until after we checked out to repair the hinge. We hope the hinge was repaired before the next guest checked in. 2) The toilet flush handle was slightly cracked but still functional. We forgot to notify the staff; it was barely noticeable. 3) The guest or owner in the room above our room walked very loudly. We were used to hearing noises from people walking in the hall but this was our first time hearing footsteps through the ceiling. Other than those three items, our stay was excellent. The front desk staff were courteous and helpful. The housekeeping crew were unobtrusive. The long driveway to the ample parking lot gives enough distance from the busy"

More cheap stays in Chester

Riverdale Inn

1500 Riverdale Street West Springfield MA

￥12,225

￥13,992 total

Jun 21 - Jun 22

includes taxes & fees

6/10 (1,001 reviews)

Frequently asked questions

What's the best place to stay in Chester?

Berkshire Mountain Lodge, located 17.2 mi (27.7 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 Berkshires Untold and Quality Inn West Springfield. See all available top hotels, or vacation rentals in Chester.

What are some of the best vacation rentals in Chester?

Cozy Riverside Berkshires Retreat: This vacation home rental outside of Chester is located on a river and has a fireplace, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and kitchenware, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games. See all 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'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. There are 870 hotels and other accommodations in the surrounding area. 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 Glendale Falls 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.

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Our top choices for Chester hotels

Riverdale Inn

Hampton Inn Westfield

Fairfield Inn & Suites Springfield Holyoke

D. Hotel Suites & Spa

Candlewood Suites West Springfield by IHG

Best Western Springfield West Inn

Red Roof Inn PLUS+ West Springfield

Best Western Plus Berkshire Hills Inn & Suites

Quality Inn Westfield - Springfield

Hampton Inn West Springfield

River Valley Inn

Baldwin Inn & Suites, SureStay Collection by Best Western

Tru by Hilton Chicopee Springfield

Residence Inn Springfield Chicopee

Hotel Northampton

FairBridge Inn Express

The Ellery

Naomi's Inn Bed & Breakfast

The Yankee Inn

Hampton Inn Chicopee/Springfield

Stay near popular Chester attractions

Chester Town Hall

Learn more about Chester

Top Chester Hotel Reviews

Quality Inn & Suites Northampton - Amherst

More cheap stays in Chester

Riverdale Inn

Frequently asked questions

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