Chesterfield Holidays

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Top Flight + Hotel Deals in Chesterfield

Price found within the past 48 hours. Click for updated prices.
The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Price was €1,114, price is now €942 per person
€942
per person
27 Dec - 31 Dec
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.2/10 Wonderful! (2,221 reviews)
Great staff and service

Reviewed on 7 Nov 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was €1,609, price is now €1,230 per person
€1,230
per person
29 Dec - 2 Jan
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (475 reviews)
So what a hotel. A small issue was handled with disproportionate kindness! The ambiance is lively, the space is luxe, the team from bellhop to GM were all exceptional. Thank you all for my short stop with you

Reviewed on 5 Nov 2025

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Price was €1,579, price is now €1,216 per person
€1,216
per person
27 Dec - 31 Dec
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.4/10 Exceptional! (522 reviews)
This hotel has it all, best in class care and service.

Reviewed on 24 Oct 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was €1,573, price is now €1,293 per person
€1,293
per person
27 Dec - 31 Dec
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (1,008 reviews)
Fantastic room, amazing premium bed! Wonderful experience for a busy business traveller

Reviewed on 6 Nov 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was €1,546, price is now €1,287 per person
€1,287
per person
27 Dec - 31 Dec
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,019 reviews)
Excellent hotel, great location, staff fantastic

Reviewed on 31 Oct 2025

Top hotels in Chesterfield

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (745 reviews)
Clean, convenience, great staff, quiet, beautiful and secluded yet close to everything! Thank you

Reviewed on 2 Nov 2025

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Berkshire Mountain Lodge
Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St, West Springfield, MA
Fully refundableReserve now, pay when you stay
The price is €89 per night from 16 Nov to 17 Nov
€89
16 Nov - 17 Nov
includes taxes & fees
7/10 Good! (1,041 reviews)
Everything was okay I think just slightly overpriced

Reviewed on 2 Nov 2025

Quality Inn West Springfield
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
Fully refundable
The price is €95 per night from 21 Nov to 22 Nov
€95
21 Nov - 22 Nov
includes taxes & fees
7.8/10 Good! (939 reviews)
Spotless and friendly staff

Reviewed on 2 Nov 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
See all 482 properties in Chesterfield
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.

Chesterfield Gorge
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.