Chesterfield Vacations from $609

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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.
Deerfield Inn

Deerfield Inn

3 out of 5
Save 100% on your flight
Price was $901, price is now $609 per person
$609
per person
Sep 3 - Sep 7
found 12 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.4/10 Exceptional! (3 reviews)
We thoroughly enjoyed all aspects of our stay. The Inn was incredibly charming and comfortable. We will definitely be back.

Reviewed on Jul 11, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $1,891, price is now $1,121 per person
$1,121
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Love coming back to a refreshed clean room after a long hot day of sightseeing.

Reviewed on Jul 15, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Save 100% on your flight
Price was $2,615, price is now $1,707 per person
$1,707
per person
Oct 5 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.4/10 Exceptional! (474 reviews)
perfecto

Reviewed on Jun 8, 2026

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
Save 100% on your flight
Price was $6,332, price is now $4,158 per person
$4,158
per person
Aug 26 - Sep 1
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
10/10 Exceptional! (9 reviews)
It was an amazing relaxing place. Very family friendly

Reviewed on Jul 12, 2026

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
Price was $1,237, price is now $816 per person
$816
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Los Angeles (QLA) to Boston (BOS)
8.4/10 Very Good! (190 reviews)
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.

Reviewed on May 19, 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

Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St West Springfield MA
Fully refundable
$90 nightly
The price is $102 total per night from Aug 6 to Aug 7
$102 total
Aug 6 - Aug 7
Total with taxes and fees
7/10 Good! (1,023 reviews)
"The air conditioning worked fine. Staff was nice. That it. Place"

Reviewed on Jul 15, 2026

Quality Inn West Springfield
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $168 total per night from Aug 16 to Aug 17
$168 total
Aug 16 - Aug 17
Total with taxes and fees
9/10 Wonderful! (1,005 reviews)
"Would definitely return. Clean, quiet and fully equipped kitchen. Great location."

Reviewed on Jul 15, 2026

Berkshire Mountain Lodge
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
Fully refundable
$142 nightly
The price is $158 total per night from Jul 26 to Jul 27
$158 total
Jul 26 - Jul 27
Total with taxes and fees
9.2/10 Wonderful! (2,144 reviews)
"This is an excellent, all around lovely hotel. The room was very clean and spacious. The staff is super helpful and friendly. There is a great breakfast with a range of items -- I am vegetarian and there were many choices -- including chickpea salad! I stayed here twice this year -- it is now my ..."

Reviewed on Jul 15, 2026

D. Hotel Suites & Spa
See all 509 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 $609 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.