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.
Fairmont Copley Plaza, Boston
Back Bay
Price was CA $1,905, price is now CA $1,311 per person
CA $1,311
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9/10 Wonderful! (1,243 reviews)
Staff were nice .
The room was not clean and the bathroom has no venting and you can’t open a window so it was not hygienic at all.
Things are old and not that greatly maintained in the rooms.
The lobby and the location are amazing
Reviewed on May 13, 2026
Furnished Apartment Near Longwood
North Brookline
Price was CA $2,690, price is now CA $1,924 per person
CA $1,924
per person
Aug 4 - Aug 10
found 24 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Boston (BOS)
7.4/10 Good! (3 reviews)
Easy to check in, students friendly apartment, convenient location, easy to call Uber or Lyft, and within 20 min. drive to the famous universities.
Reviewed on Apr 1, 2026
Chesterfield Hotel Deals
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is CA $121 per night from May 24 to May 25
CA $121
CA $165 total
May 24 - May 25
includes taxes & fees
9/10 Wonderful! (934 reviews)
Clean and great job staffing
Reviewed on May 15, 2026
Quality Inn West Springfield
1150 Riverdale St West Springfield MA
Fully refundable
The price is CA $127 per night from May 31 to Jun 1
CA $127
CA $146 total
May 31 - Jun 1
includes taxes & fees
7/10 Good! (1,014 reviews)
Everything it’s ok Awesome breakfast
Reviewed on May 14, 2026
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
The price is CA $224 per night from May 25 to May 26
CA $224
CA $262 total
May 25 - May 26
includes taxes & fees
9.2/10 Wonderful! (2,234 reviews)
Spacious room, very helpful staff, good coffee and an excellent breakfast.
Reviewed on May 16, 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.
