Chesterfield Vacations from $343

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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.
Even Hotels Manchester Airport by IHG

Even Hotels Manchester Airport by IHG

3.5 out of 5
South End
Save 100% on your flight
per person
Sep 12 - Sep 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
8.8/10 Excellent! (748 reviews)
The king suite is great

Reviewed on Jul 12, 2025

Ocean Air Suites

Ocean Air Suites

2.5 out of 5
Hampton Beach
Save 100% on your flight
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Boston (BOS)
9.2/10 Wonderful! (32 reviews)
location was awesome. able to see fireworks right from deck in the back. It’s definitely family friendly would definitely be coming back again next year :)

Reviewed on Sep 3, 2024

Sunbird ANNEX Resort

Sunbird ANNEX Resort

2 out of 5
Save 100% on your flight
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Boston (BOS)
7.8/10 Good! (715 reviews)
It’s my favorite place to go check list

Reviewed on Jul 10, 2025

The Cove At Salem

The Cove At Salem

3 out of 5
Save 100% on your flight
per person
Sep 12 - Sep 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.4/10 Exceptional! (576 reviews)
Very clean. The room is decorated in a very stylish manner that goes with the theme of the city. Located conveniently within walking distance to the city center.

Reviewed on Jul 11, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Sep 26 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Great hotel terrific staff

Reviewed on Jul 12, 2025

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Discover the most popular places to visit in Chesterfield

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.

Chesterfield Gorge

Chesterfield Hotel Deals

Hotel UMass
Hotel UMass
2.5 out of 5
1 Campus Center Way, Amherst, MA
Fully refundableReserve now, pay when you stay
$180 nightly
The price is $201 total per night from Jul 23 to Jul 24
$201 total
Jul 23 - Jul 24
Total includes taxes and fees
8.6/10 Excellent! (1,007 reviews)
"Nice and clean hotel in the center of UMass."

Reviewed on Jul 11, 2025

Hotel UMass
Quality Inn West Springfield
Quality Inn West Springfield
2.5 out of 5
1150 Riverdale St, West Springfield, MA
Fully refundableReserve now, pay when you stay
$86 nightly
The price is $99 total per night from Jul 20 to Jul 21
$99 total
Jul 20 - Jul 21
Total includes taxes and fees
7/10 Good! (1,006 reviews)
"Safe and convenient"

Reviewed on Jul 11, 2025

Quality Inn West Springfield
D. Hotel Suites & Spa
D. Hotel Suites & Spa
3 out of 5
1 Country Club Rd, Holyoke, MA
Fully refundable
$134 nightly
The price is $150 total per night from Jul 13 to Jul 14
$150 total
Jul 13 - Jul 14
Total includes taxes and fees
9.2/10 Wonderful! (2,268 reviews)
"We’ve stayed here for many many years but this trip our mattress was way past needing to be replaced we both ended up in middle. The pillow cases only covered like 3/4 of the pillow so maybe buy the right size. Overall we love the hotel but it does seem to be trending down as far as cleanliness and ..."

Reviewed on Jul 10, 2025

D. Hotel Suites & Spa
See all 462 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 $343 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.