Chesterfield Vacations from $617

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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.
Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
Save 100% on your flight
Price was $1,013, price is now $617 per person
$617
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9/10 Wonderful! (2,071 reviews)
Very professional staff Clean Very nice ambience

Reviewed on Oct 30, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $1,505, price is now $912 per person
$912
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)

Delamar West Hartford

Delamar West Hartford

4 out of 5
Price was $1,170, price is now $797 per person
$797
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
9.8/10 Exceptional! (1,003 reviews)
We liked that it was right downtown within walking distance to Restaurants and Shopping and Valet Parking was a plus. Breakfast was great! We will stay here again! Thank you!

Reviewed on Oct 30, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was $1,658, price is now $1,141 per person
$1,141
per person
Jan 21 - Jan 24
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.4/10 Exceptional! (491 reviews)

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was $1,091, price is now $787 per person
$787
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)

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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
$113 nightly
The price is $126 total per night from Nov 30 to Dec 1
$126 total
Nov 30 - Dec 1
Total with taxes and fees
9/10 Wonderful! (1,247 reviews)
"The coffee station is very unfriendly. You can only make a cup of coffee at a time. And when you have one family with multiple people it takes too much time to get one single cup of coffee so you have people frustrated. They were also draining the pool with no notification to the people staying ..."

Reviewed on Oct 30, 2026

Berkshire Mountain Lodge
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
Fully refundable
$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
Fully refundable
$129 nightly
The price is $144 total per night from Nov 30 to Dec 1
$144 total
Nov 30 - Dec 1
Total with taxes and fees
Hotel UMass
See all 517 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 $617 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.