Chesterfield Holidays
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Top Flight + Hotel Deals in Chesterfield
Price found within the past 48 hours. Click for updated prices.
Fairmont Copley Plaza, Boston
Back Bay
Price was €1,257, price is now €975 per person
€975
per person
25 Jan - 30 Jan
found 10 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (1,094 reviews)
The room appeared clean but in trying to plug in charging cables I discovered a Qtip under the bedside table. Other than that, the staff was helpful, room service rapid and helpful and all courteous.
Reviewed on 22 Dec 2025
Boston Harbor Hotel
North End
Price was €2,499, price is now €1,426 per person
€1,426
per person
25 Jan - 30 Jan
found 10 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Everything was wonderful including a delicious breakfast. We will definitely return.
Reviewed on 17 Dec 2025
The Newbury Boston
Back Bay
Price was €1,770, price is now €1,312 per person
€1,312
per person
25 Jan - 30 Jan
found 10 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.4/10 Exceptional! (536 reviews)
Very friendly staff. Amazing location. The room was perfect. Didn’t go to Contessa, but we ran into the Chef in the elevator and he was super fun and courteous. The bar is cool, we ate there a couple nights. We had a very pleasant Thanksgiving week there. Festive and lively hotel. There’s Tatte around the corner and every store you can think of within walking distance. Looking forward to our next stay!
Reviewed on 4 Dec 2025
Top hotels in Chesterfield
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
The price is €108 per night from 22 Jan to 23 Jan
€108
22 Jan - 23 Jan 2026
includes taxes & fees
9.2/10 Wonderful! (2,259 reviews)
Everything was perfect.
Reviewed on 17 Dec 2025
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Fully refundable
The price is €88 per night from 25 Dec to 26 Dec
€88
25 Dec - 26 Dec
includes taxes & fees
8/10 Very Good! (995 reviews)
While waiting for our vallet car due to construction. The hotel staff were engaging and had personal conversations with us. Rooms were good and all staff treated us exceptional. Give them an atta boy on proformance
Reviewed on 22 Dec 2025
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
The price is €113 per night from 11 Jan to 12 Jan
€113
11 Jan - 12 Jan 2026
includes taxes & fees
9/10 Wonderful! (793 reviews)
Spacious room and loved pool and hot tub!
Reviewed on 19 Dec 2025
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.
Popular places to visit
Chesterfield Gorge
Explore the great outdoors at Chesterfield Gorge, a lovely green space in Chesterfield. Wander the lakeside and forests while you're in the area.
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- Becket Land Trust Historic Quarry
- Visit Sherwood Forest
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- Visit Charlemont
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
