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.
Eurostars The Boxer
West End
Price was CA $2,173, price is now CA $1,337 per person
CA $1,337
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (1,426 reviews)
Location, location, location! Breakfast is top notch. The entire staff was helpful and friendly.
Reviewed on Apr 3, 2026
The Inn at Hastings Park, Relais & Chateaux - Boston
Price was CA $2,592, price is now CA $1,604 per person
CA $1,604
per person
Jun 17 - Jun 21
found 12 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Boston (BOS)
9.6/10 Exceptional! (252 reviews)
Excellent experience- clean and very helpful staff
Reviewed on Mar 9, 2026
The Langham, Boston
Downtown Boston
Price was CA $3,781, price is now CA $2,429 per person
CA $2,429
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
The rooms were very clean, beds were comfortable, staff friendly and great amenities (I wish the pool was open until 10 pm).
Reviewed on Apr 4, 2026
Chesterfield Hotel Deals
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
The price is CA $171 per night from Apr 20 to Apr 21
CA $171
CA $199 total
Apr 20 - Apr 21
includes taxes & fees
9.4/10 Exceptional! (2,228 reviews)
❤️
Reviewed on Apr 6, 2026
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 6 to May 7
CA $121
CA $166 total
May 6 - May 7
includes taxes & fees
9/10 Wonderful! (895 reviews)
Love that place. Does need a little sprucing up. Staff great and accomodating
Reviewed on Apr 5, 2026
Comfort Inn & Suites Hadley - Amherst
400 Russell St Hadley MA
Fully refundable
The price is CA $177 per night from Apr 20 to Apr 21
CA $177
CA $197 total
Apr 20 - Apr 21
includes taxes & fees
9.2/10 Wonderful! (1,009 reviews)
Excellent breakfast for a quick unexpected benefit
Reviewed on Apr 5, 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.
