Chesterfield Vacations from $589

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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.

The Latest Chesterfield vacation packages

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $1,333, price is now $589 per person
$589
per person
Jan 7 - Jan 12
found 5 hours ago
Roundtrip flight included
San Diego (SAN) to Boston (BOS)
8.4/10 Very Good! (190 reviews)
The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.

Reviewed on Oct 17, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,518, price is now $870 per person
$870
per person
Jan 6 - Jan 9
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)
Excellent as always.

Reviewed on Oct 27, 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $1,562, price is now $1,030 per person
$1,030
per person
Dec 10 - Dec 13
found 2 hours ago
Roundtrip flight included
Dallas (DAL) to Boston (BOS)
9.6/10 Exceptional! (343 reviews)
设施很新，SPA桑拿体验特别好，晚餐气氛很棒

Reviewed on Oct 20, 2026

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $2,888, price is now $2,045 per person
$2,045
per person
Dec 17 - Dec 23
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
9.4/10 Exceptional! (465 reviews)

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was $1,197, price is now $872 per person
$872
per person
Dec 10 - Dec 13
found 3 hours ago
Roundtrip flight included
Dallas (DAL) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)
Excellent experience

Reviewed on Oct 22, 2026

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Stay near popular Chesterfield attractions

Chesterfield Gorge

Explore the great outdoors at Chesterfield Gorge, a lovely green space in Chesterfield. Wander the lakeside and forest while you're in the area.
See properties

Chesterfield Hotel Deals

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$115 nightly
The price is $128 total per night from Nov 25 to Nov 26
$128 total
Nov 25 - Nov 26
Total with taxes and fees
9/10 Wonderful! (1,233 reviews)
"The sink drain didn’t work."

Reviewed on Oct 26, 2026

Berkshire Mountain Lodge
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
$118 nightly
The price is $131 total per night from Nov 1 to Nov 2
$131 total
Nov 1 - Nov 2
Total with taxes and fees
D. Hotel Suites & Spa
Hotel UMass

Hotel UMass

2.5 out of 5
1 Campus Center Way Amherst MA
$144 nightly
The price is $161 total per night from Nov 27 to Nov 28
$161 total
Nov 27 - Nov 28
Total with taxes and fees
Hotel UMass
See all 511 properties in Chesterfield
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.

Find the Best Chesterfield Vacation Packages

Chesterfield Essential Information

Language
English
Currency
U.S dollars
Population
1,200
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Historic Northampton, Academy of Music Theater and Calvin Theatre and Performing Arts Center

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Frequently asked questions

How much does a Chesterfield vacation package cost?
You'll find cheap prices from $589 on Expedia for your Chesterfield getaway. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Chesterfield costs.
What are the cheapest months to go to Chesterfield?
November, December and January are the best times to search for cheap Chesterfield vacation packages. Opting to travel in less busy months means you can typically find better prices on accommodations and flights.
How many days is enough for Chesterfield?
With a well-organized travel plan, you can easily tick off the most popular Chesterfield attractions in a handful of days. But if you'd like to explore off the beaten track or go on day tours, think about booking your Chesterfield vacation for longer.
How to find the best Chesterfield package deals?
Landing a cheap Chesterfield package deal is a cinch with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Chesterfield package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Chesterfield vacation as a package?
You can enjoy significant savings on your next Chesterfield retreat by booking a personalized vacation package. Click on the "Package" heading, then enter your travel dates and destination to see some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Chesterfield?
If you have your Chesterfield vacation dates finalized, book early to grab some incredible deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are great for quick escapes.
Does Expedia offer Book Now, Pay Later Chesterfield vacation packages?
Your Chesterfield break should be a relaxing escape from your busy life, not a source of money-related stress. So to give you more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.

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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.