Chesterfield Holidays
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Top Flight + Hotel Deals in Chesterfield
Price found within the past 48 hours. Click for updated prices.
The Charles Hotel
West Cambridge
Save 100% on your flight
Price was €1,478, price is now €993 per person
€993
per person
23 Nov - 30 Nov
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.4/10 Exceptional! (1,005 reviews)
I had a lovely stay at this hotel. Very nice atmosphere and close to many restaurants, shopping, and Harvard campus. Although I did not need parking, there was also an on-premise parking lot. Staff were kind and accommodating. My only issue was that the hotel has shows on the 3rd floor and I could hear the music at night from my room on the 4th FL so beware if you are a light sleeper. Otherwise, I would certainly stay here again when in the Cambridge area.
Reviewed on 17 Sept 2025
Boston Harbor Hotel
North End
Save 100% on your flight
Price was €2,604, price is now €1,723 per person
€1,723
per person
23 Oct - 27 Oct
found 1 day ago
Return flight included
Shannon (SNN) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
This is one of the nicest hotels I’ve stayed in—it’s a beautiful, well-located property with top-notch front desk staff and many thoughtful extras.
Reviewed on 18 Sept 2025
Raffles Boston
Back Bay
Save 100% on your flight
Price was €2,491, price is now €1,723 per person
€1,723
per person
23 Oct - 27 Oct
found 1 day ago
Return flight included
Shannon (SNN) to Boston (BOS)
9.8/10 Exceptional! (160 reviews)
Best hotel in Boston without question! The staff are exceptional, very friendly and attentive. The masseuses at the spa, especially (I believe her name was) Paula are very skilled and helpful with sore muscles and joints after traveling. La Padrona, Amar, and The Long Bar all have delicious food. I will definitely be back!
Reviewed on 15 Sept 2025
The Whitney Hotel
Beacon Hill
Save 100% on your flight
Price was €1,668, price is now €1,234 per person
€1,234
per person
23 Nov - 30 Nov
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (457 reviews)
Everything about this place is right! One of the nicest hotels we've ever stayed at.
Reviewed on 5 Sept 2025
Top hotels in Chesterfield
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
The price is €94 per night from 24 Sept to 25 Sept
€94
24 Sept - 25 Sept
includes taxes & fees
8.8/10 Excellent! (653 reviews)
"It was a great Stay where we had to it was a good area I would come back to this place again"
Reviewed on 21 Sept 2025
Red Roof Inn PLUS+ West Springfield
1254 Riverdale Street, West Springfield, MA
Fully refundableReserve now, pay when you stay
The price is €86 per night from 2 Oct to 3 Oct
€86
2 Oct - 3 Oct
includes taxes & fees
6.8/10 (1,016 reviews)
"."
Reviewed on 22 Sept 2025
Quality Inn West Springfield
1150 Riverdale St, West Springfield, MA
Fully refundableReserve now, pay when you stay
The price is €96 per night from 5 Oct to 6 Oct
€96
5 Oct - 6 Oct
includes taxes & fees
7/10 Good! (1,025 reviews)
"The hotel was absolutely spotless, the staff was perfect, the breakfast was OK. The only drawback is being right next the highway. The noise from the passing vehicles prevented a good night's sleep. This is of no fault of the hotel or the staff but it is something to take into consideration."
Reviewed on 17 Sept 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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