Chesterfield Vacation Packages
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Your Chesterfield Vacation
Skip the stress of organizing your next big adventure with a Chesterfield vacation package. Whether you're in town for its art, food, architecture or something else, this city offers countless exciting experiences to delve into. A trip to Chesterfield is an excellent opportunity to take in the sights. Check out renowned attractions like Chesterfield Gorge, Swift River and Petticoat Hill. Your perfect Chesterfield vacation is just clicks away. Explore hotels, flights and more on Expedia for a trip that's tailored to suit your style.
Top Chesterfield Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Inn at Hastings Park, Relais & Chateaux - Boston
Price was CA $2,468, price is now CA $1,570 per person
CA $1,570
per person
Jun 13 - Jun 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (252 reviews)
Excellent experience- clean and very helpful staff
Reviewed on Mar 9, 2026
Eurostars The Boxer
West End
Price was CA $2,230, price is now CA $1,466 per person
CA $1,466
per person
May 21 - May 27
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
8.6/10 Excellent! (1,395 reviews)
Great hotel, in the middle of downtown, walking distance from td garden, friendly staff and great amenities, will be back for sure
Reviewed on Mar 30, 2026
The Inn on Arsenal
Price was CA $2,342, price is now CA $1,667 per person
CA $1,667
per person
Jun 13 - Jun 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.2/10 Very Good! (84 reviews)
It was a great place to stay for the night. Clean and professional. The only complaint is that the bathroom door didn’t close completely and the heater was really loud.
Reviewed on Mar 28, 2026
Chesterfield Hotel Deals
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
The price is CA $171 per night from Apr 14 to Apr 15
CA $171
CA $199 total
Apr 14 - Apr 15
includes taxes & fees
9.4/10 Exceptional! (2,229 reviews)
The room was not very clean. When I spoke with staff about it they were not very nice or helpful.
Reviewed on Mar 31, 2026
Comfort Inn & Suites Hadley - Amherst
400 Russell St Hadley MA
The price is CA $187 per night from Apr 14 to Apr 15
CA $187
CA $209 total
Apr 14 - Apr 15
includes taxes & fees
9.2/10 Wonderful! (1,007 reviews)
Clean room and sufficient place to sleep. The pillows were comfortable and the staff were very polite. We appreciated the GF options for breakfast and the small fitness center. We had a nice dinner at a location recommend by the hotel as well.
Reviewed on Mar 30, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is CA $120 per night from Apr 30 to May 1
CA $120
CA $165 total
Apr 30 - May 1
includes taxes & fees
9/10 Wonderful! (891 reviews)
Easy to book, clean room, close to entertainment and restaurants, has a pool and hot tub.
Reviewed on Mar 31, 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.
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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.
