
Chesterfield Holidays
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Top Flight + Hotel Deals in Chesterfield
Price found within the past 48 hours. Click for updated prices.


Hotel Ivy Boston Common
Bay Village
Price was €1,914, price is now €1,230 per person
€1,230
per person
10 Jun - 13 Jun
found 3 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
8.4/10 Very Good! (1,441 reviews)
I was only here because I had an early flight out of Boston the next morning. I arrived way past standard check in time (3-4 pm), and the staff were very communicative, friendly and understanding. The room did the trick for just an overnight. Comfortable beds with comfortable pillows. Loved the bathroom. Loved the lighting. Only thing to note for future travelers that may be “negative”: The pictures make the room look much bigger than it is, like the size of a standard hotel room. It is about 1/4 of the size of a normal hotel room. At least this was the case for my room.
Reviewed on 6 May 2026

The Langham, Boston
Downtown Boston
Price was €2,436, price is now €1,580 per person
€1,580
per person
10 Jun - 14 Jun
found 3 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (1,007 reviews)
Service both at the hotel and restaurants was the one of the best experiences I’ve had
Reviewed on 2 May 2026

Boston Harbor Hotel
North End
Price was €2,388, price is now €1,690 per person
€1,690
per person
10 Jun - 13 Jun
found 3 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
They're always my hands down favorite in Boston! Thanks for being so lovely!!
Reviewed on 5 May 2026

Revere Hotel Boston Common
Bay Village
Price was €1,606, price is now €1,291 per person
€1,291
per person
10 Jun - 14 Jun
found 3 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (1,990 reviews)
The pace was very nice easy to get wherever you wanted to go. The subway was a quick walk that could get you all over. All the staff was very friendly. The housekeeping done a great job daily
Reviewed on 5 May 2026
Top hotels in Chesterfield

Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is €102 per night from 24 May to 25 May
€102
24 May - 25 May
includes taxes & fees
9/10 Wonderful! (925 reviews)
Room very spacious and clean. Full kitchen is a great bonus.
Reviewed on 4 May 2026

Hotel UMass
1 Campus Center Way Amherst MA
Fully refundable
The price is €121 per night from 10 May to 11 May
€121
10 May - 11 May
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
It was good! Great location!
Reviewed on 5 May 2026

D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
The price is €168 per night from 21 May to 22 May
€168
21 May - 22 May
includes taxes & fees
9.2/10 Wonderful! (2,218 reviews)
The room was massive and roomy. The floor was shiny and clean. Everything was tidy. The bed and pillows were comfortable.
Reviewed on 6 May 2026
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.
