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



Raffles Boston
Back Bay
Save 100% on your flight
per person
19 Sept - 22 Sept
found 20 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (135 reviews)
I had high expectations since we have been to Raffles Singapore before and after the recent renovations and it is one of our favorite hotels in the world! Glad to say that Raffles Boston did not disappoint. The hotel decor is gorgeous, thoughtfully luxurious in every detail. Location is great. Service is professional but friendly. The room butler is a convenience that cannot be overstated. Also, the first hotel that actually kept the room temperature at 66 F during the whole night. Adios, Four Seasons! Raffles is my new home in Boston.
Reviewed on 5 Aug 2025


The Whitney Hotel
Beacon Hill
per person
19 Sept - 22 Sept
found 20 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (428 reviews)
Had an amazing time at the Whitney. Front desk service was impeccable, friendly and was ‘just’ the added touch I would expect of a property of this caliber. I really do look forward to my next time in Boston and hope to stay at the Whitney.
Reviewed on 25 Jul 2025
Top hotels in Chesterfield

Quality Inn West Springfield
1150 Riverdale St, West Springfield, MA
Fully refundableReserve now, pay when you stay
The price is €91 per night from 24 Aug to 25 Aug
€91
24 Aug - 25 Aug
includes taxes & fees
7/10 Good! (1,002 reviews)
"My daughter and the kids said it was perfect for their overnight stay after visiting Six Flags."
Reviewed on 7 Aug 2025

Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (543 reviews)
"Very spacious room with full kitchen. Definitely worth the price. Would use again"
Reviewed on 5 Aug 2025

D. Hotel Suites & Spa
1 Country Club Rd, Holyoke, MA
Fully refundableReserve now, pay when you stay
The price is €129 per night from 11 Aug to 12 Aug
€129
11 Aug - 12 Aug
includes taxes & fees
9.2/10 Wonderful! (2,239 reviews)
"Nice hotel with mediocre breakfast"
Reviewed on 1 Aug 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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