Top 10 Hotels in Chester, MA from ￥10,081 - Competitive Prices

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Our top choices for Chester hotels

Family House | Private kitchen | Coffee/tea maker, fridge, microwave

1. Becket Motel

Becket

Paul

￥15,423

￥22,463 total

includes taxes & fees

Sep 7 - Sep 8

Executive King Room | Premium bedding, desk, blackout drapes, iron/ironing board

2. D. Hotel Suites & Spa

Holyoke

Kerri

￥19,007

￥22,239 total

includes taxes & fees

Sep 9 - Sep 10

Room, Accessible, Non Smoking | In-room safe, desk, blackout drapes, iron/ironing board

3. Hampton Inn West Springfield

West Springfield

Matthew

￥15,376

￥17,597 total

includes taxes & fees

Sep 10 - Sep 11

2 full Extra Long Beds | Desk, laptop workspace, WiFi (free)

4. Berkshire Lake Lodge

Lee

mike

￥21,482

￥23,995 total

includes taxes & fees

Sep 7 - Sep 8

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

5. Hampton Inn Westfield

Westfield

Mykola

￥18,221

￥20,354 total

includes taxes & fees

Oct 7 - Oct 8

Standard Room, 1 King Bed, Non Smoking | Desk, iron/ironing board, cribs (surcharge), rollaway beds (surcharge)

6. Quality Inn Lee - Lenox South

Lee

Christine

￥15,806

￥17,654 total

includes taxes & fees

Sep 27 - Sep 28

Studio Suite, Multiple Beds | Desk, laptop workspace, WiFi (free), bed sheets

Deluxe Room, 1 King Bed | Bathroom | Hair dryer, towels, soap, shampoo

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

7. River Valley Inn

West Hatfield

Michael

￥13,898

￥15,525 total

includes taxes & fees

Sep 14 - Sep 15

Room, 2 Double Beds | Hypo-allergenic bedding available, in-room safe, desk, laptop workspace

8. Hotel Northampton

Northampton

steven

￥19,337

￥21,600 total

includes taxes & fees

Sep 7 - Sep 8

Standard Room, 1 King Bed, Non Smoking | Pillowtop beds, in-room safe, desk, blackout drapes

9. Quality Inn Westfield - Springfield

Westfield

Thomas

￥15,806

￥17,656 total

includes taxes & fees

Oct 4 - Oct 5

Standard Room, 2 Double Beds, Non Smoking | Desk, iron/ironing board, WiFi (free), bed sheets

10. Best Western Springfield West Inn

West Springfield

Luz

￥15,937

￥18,240 total

includes taxes & fees

Sep 13 - Sep 14

Premium bedding, down comforters, blackout drapes, iron/ironing board

11. Tru by Hilton Chicopee Springfield

Chicopee

Leon

￥19,092

￥21,659 total

includes taxes & fees

Sep 13 - Sep 14

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, desk, laptop workspace, blackout drapes

In-room safe, desk, laptop workspace, blackout drapes

12. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Prasanna

￥14,050

￥15,694 total

includes taxes & fees

Sep 8 - Sep 9

Premium bedding, pillowtop beds, in-room safe, desk

13. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

BJORN

￥20,626

￥23,039 total

includes taxes & fees

Sep 15 - Sep 16

14. La Quinta Inn & Suites by Wyndham Springfield MA

Metro Center

Meris

￥18,462

￥20,946 total

includes taxes & fees

Sep 8 - Sep 9

15. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

Bruce

￥25,103

￥28,040 total

includes taxes & fees

Sep 10 - Sep 11

Down comforters, desk, laptop workspace, iron/ironing board

16. Hampton Inn Chicopee/Springfield

Chicopee

Margaret

￥20,337

￥23,072 total

includes taxes & fees

Sep 20 - Sep 21

In-room safe, desk, laptop workspace, iron/ironing board

17. Howard Johnson by Wyndham Lenox

Lenox

irene

￥12,345

￥13,790 total

includes taxes & fees

Sep 7 - Sep 8

Grand Villa, 3 Bedrooms | Iron/ironing board, cribs (free), WiFi, bed sheets

18. Holiday Inn Club Vacations Oak 'n Spruce Resort

South Lee

Linda

￥16,032

￥20,964 total

includes taxes & fees

Sep 14 - Sep 15

19. Quality Inn West Springfield

West Springfield

Magaly

￥13,834

￥15,832 total

includes taxes & fees

Oct 4 - Oct 5

Standard Room, 1 King Bed (Smoke Free) | Pillowtop beds, desk, blackout drapes, WiFi (free)

20. Red Roof Inn PLUS+ West Springfield

West Springfield

Chris

￥16,033

￥18,350 total

includes taxes & fees

Oct 4 - Oct 5

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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 theater in Chester!

See all hotels in Chester

A stone bridge over a flowing river with rocks and autumn foliage.

Top Chester Hotel Reviews

D. Hotel Suites & Spa

8/10 Good

"This is a beautiful spot, along the river just outside the city. It’s close to everything but away from the hustle and bustle so it’s quiet and it feels secluded. The property is a bit dated but the rooms are kept up with more modern decor. It was perfect for our stay, and we’ll definitely be back again."

Tru by Hilton Chicopee Springfield

10/10 Excellent

"Great stay, breakfast was ok, busy week loud neighbor. But great place"

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent

"New facility. Everything was exceptionally clean. Fabulous and helpful staff."

Berkshire Mountain Lodge

10/10 Excellent

"We were there for a one night stay after a show at Tanglewood. Being able to check in online in advance was excellent and saved us a lot of time. There were three of us traveling (a couple and a family member) so we requested a suite. It was huge, well appointed and so clean. The cost was incredibly reasonable for the amount of space we had! The king bed in its own bedroom was super comfortable, and the pull out couch did the job. We didn’t use any of the extra amenities, but saw a few families with children. Lots of space to roam and wander, both inside and on the property. It was an easy 15 minute drive to Tanglewood, so the location worked great for us. The only negative comment would be there was no do not disturb tag for the door, so housekeeping arrived an hour before checkout and we had to send them away. We will stay again if we are in the area, highly recommended!"

Candlewood Suites West Springfield by IHG

8/10 Good

"The room is big."

The Red Lion Inn

10/10 Excellent

"Charming, updated throughout. Extremely clean and well appointed. Extremely delightful stay."

FairBridge Inn Express

8/10 Good

"The exterior is scary. The lobby is a fright. Rooms however were clean and updated. I appreciate that. But the lot is a disgrace."

More cheap stays in Chester

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

￥9,025

￥10,081 total

Oct 7 - Oct 8

includes taxes & fees

5.4/10 (892 reviews)

Quality Inn West Springfield

1150 Riverdale St West Springfield MA

￥13,834

￥15,832 total

Oct 4 - Oct 5

includes taxes & fees

7.2/10 Good! (1,017 reviews)

Blue A Modern Hotel, an Ascend Collection Hotel

1080 Riverdale St West Springfield MA

￥17,134

￥19,609 total

Oct 5 - Oct 6

includes taxes & fees

The Yankee Inn

461 Pittsfield Rd Lenox MA

￥18,126

￥20,247 total

Sep 22 - Sep 23

includes taxes & fees

Quality Inn & Suites Northampton - Amherst

117 Conz St Northampton MA

￥19,790

￥22,105 total

Oct 4 - Oct 5

includes taxes & fees

7.2/10 Good! (1,001 reviews)

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

1055 South Street Pittsfield MA

￥19,845

￥22,167 total

Sep 10 - Sep 11

includes taxes & fees

9.2/10 Wonderful! (193 reviews)

Frequently asked questions

What's the best place to stay in Chester?

Quality Inn West Springfield, located 20.6 mi (33.1 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 D. Hotel Suites & Spa and Berkshire Mountain Lodge. See all available top hotels, or vacation rentals in Chester.

What are some of the best vacation rentals in Chester?

Experience Three Sisters Sanctuary in Goshen, MA: This vacation home rental outside of Chester is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay. 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 880 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 Becket Land Trust Historic Quarry and Jacob's Pillow 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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Find hotels in Chester, MA from ￥10,081

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chester

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for Chester hotels

1. Becket Motel

2. D. Hotel Suites & Spa

3. Hampton Inn West Springfield

4. Berkshire Lake Lodge

5. Hampton Inn Westfield

6. Quality Inn Lee - Lenox South

7. River Valley Inn

8. Hotel Northampton

9. Quality Inn Westfield - Springfield

10. Best Western Springfield West Inn

11. Tru by Hilton Chicopee Springfield

12. Best Western Plus Berkshire Hills Inn & Suites

13. Holiday Inn Express Hotel & Suites Great Barrington by IHG

14. La Quinta Inn & Suites by Wyndham Springfield MA

15. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

16. Hampton Inn Chicopee/Springfield

17. Howard Johnson by Wyndham Lenox

18. Holiday Inn Club Vacations Oak 'n Spruce Resort

19. Quality Inn West Springfield

20. Red Roof Inn PLUS+ West Springfield

Stay near popular Chester attractions

Chester Town Hall

Learn more about Chester

Top Chester Hotel Reviews

D. Hotel Suites & Spa

Tru by Hilton Chicopee Springfield

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Berkshire Mountain Lodge

Candlewood Suites West Springfield by IHG

The Red Lion Inn

FairBridge Inn Express

More cheap stays in Chester

FairBridge Inn Express

Quality Inn West Springfield

Blue A Modern Hotel, an Ascend Collection Hotel

The Yankee Inn

Quality Inn & Suites Northampton - Amherst

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Frequently asked questions

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