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Hotels in Chesterfield

Choose from 508 Chesterfield Hotel Deals

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
  • 24 min walk from Chesterfield Gorge
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (931 reviews)
These are all 1 bedroom suites. There was plenty of room in kitchen cupboards for our groceries. The kitchen was well supplied with cooking utensils, dishes and glassware. The location is excellent with several grocery stores and restaurants close by. Everything was perfect except for the height ...

Reviewed on May 11, 2026

Berkshire Mountain Lodge
Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St West Springfield MA
  • 43 min drive from Chesterfield Gorge
Book a stay at this golf hotel in West Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
7/10 Good! (1,011 reviews)
Breakfast on schedule ac worked the room was ok you could hear talking all night walls were like paper the balcony was dirty glass doors would not open easily and glass was dirty to housekeeping were more friendly better than the front desk Asian lady was a little hostile I won't go back there wasn't ...

Reviewed on May 12, 2026

Quality Inn West Springfield
Hotel UMass

Hotel UMass

2.5 out of 5
1 Campus Center Way Amherst MA
  • 10 min walk from Chesterfield Gorge
Stay at this hotel in Amherst. Enjoy free breakfast, free WiFi, and 5 coffee shops/cafes. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.8/10 Excellent! (1,016 reviews)
accessible to campus

Reviewed on May 12, 2026

Hotel UMass
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
  • 20 min drive from Chesterfield Gorge
Book a stay at this spa hotel in Holyoke. Enjoy a full-service spa, 2 restaurants, and room service. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (2,230 reviews)
Perfect

Reviewed on May 12, 2026

D. Hotel Suites & Spa
Quality Inn & Suites Northampton - Amherst

Quality Inn & Suites Northampton - Amherst

2.5 out of 5
117 Conz St Northampton MA
  • 14 min drive from Chesterfield Gorge
Book a stay at this business-friendly hotel in Northampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.2/10 Good! (1,006 reviews)
Enjoyed my stay. Staff and room were excellent

Reviewed on May 11, 2026

Quality Inn & Suites Northampton - Amherst
Comfort Inn & Suites Hadley - Amherst

Comfort Inn & Suites Hadley - Amherst

2.5 out of 5
400 Russell St Hadley MA
  • 6 min drive from Chesterfield Gorge
Book a stay at this business-friendly hotel in Hadley. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9.4/10 Exceptional! (1,011 reviews)
Polite and helpful staff!

Reviewed on May 5, 2026

Comfort Inn & Suites Hadley - Amherst
Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst

2.5 out of 5
9 Greenfield Rd South Deerfield MA
  • 13 min drive from Chesterfield Gorge
Stay at this hotel in South Deerfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
7.2/10 Good! (1,009 reviews)
Hallway smelt like someone smoking pot. Bed was old and not comfortable.

Reviewed on May 11, 2026

Red Roof Inn PLUS+ South Deerfield – Amherst
The Ellery

The Ellery

3.5 out of 5
259 Elm Street Northampton MA
  • 12 min drive from Chesterfield Gorge
Stay at this hotel in Northampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
9.2/10 Wonderful! (1,013 reviews)
Everything was perfect for our first stay at the Ellery!

Reviewed on May 12, 2026

The Ellery
Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

2.5 out of 5
440 Memorial Dr Chicopee MA
  • 38 min drive from Chesterfield Gorge
Stay at this hotel in Chicopee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
9/10 Wonderful! (1,020 reviews)
Lo mejor de lo mejor, me volvería a quedar miles y miles de veces.

Reviewed on May 12, 2026

Tru by Hilton Chicopee Springfield
Blue – A Modern Hotel, an Ascend Collection Hotel

Blue – A Modern Hotel, an Ascend Collection Hotel

2.5 out of 5
1080 Riverdale St West Springfield MA
  • 44 min drive from Chesterfield Gorge
Book a stay at this business-friendly hotel in West Springfield. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions MGM Springfield ...
9.6/10 Exceptional! (194 reviews)
The staff were very friendly. The room was clean and the massaging chair in the room was awesome after a long day of traveling.

Reviewed on May 11, 2026

Blue – A Modern Hotel, an Ascend Collection Hotel
Hampton Inn West Springfield

Hampton Inn West Springfield

2.5 out of 5
1011 Riverdale St West Springfield MA
  • 44 min drive from Chesterfield Gorge
Book a stay at this business-friendly hotel in West Springfield. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,003 reviews)
This place is seriously dated and needs a total makeover. Surprised that Hilton hasn’t stepped in on this.

Reviewed on May 3, 2026

Hampton Inn West Springfield
Courtyard by Marriott Hadley Amherst

Courtyard by Marriott Hadley Amherst

3 out of 5
423 Russell St Hadley MA
  • 6 min drive from Chesterfield Gorge
Book a stay at this business-friendly hotel in Hadley. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
9/10 Wonderful! (725 reviews)
Clean room and hotel, great breakfast options. Wish I could stay longer!

Reviewed on May 1, 2026

Courtyard by Marriott Hadley Amherst
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.

Find cheap hotels in Chesterfield

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Frequently Asked Questions About Chesterfield hotels

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How many hotels are there in Chesterfield?

With over 508 hotels in Chesterfield, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $106.

How to find cheap car rentals in Chesterfield?

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