Chesterfield Vacations from $696

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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.
Studio Allston Hotel

Studio Allston Hotel

3.5 out of 5
Brighton
Save 100% on your flight
per person
Aug 18 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
8.6/10 Excellent! (1,018 reviews)
Studio Alliston is a tired hotel. The staff are a mixed bag and slow. The room was dingey and smelled funny. Id stay elsewhere next time.

Reviewed on Jun 15, 2025

Holly Tree Resort

Holly Tree Resort

3 out of 5
Save 100% on your flight
per person
Aug 18 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (343 reviews)
Very nice place to stay

Reviewed on Mar 21, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Aug 6 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,007 reviews)
Location for first time Boston visitors was really good as a lot area to explore by foot then you could Uber the rest. The staff and in-room dining was outstanding

Reviewed on Jun 16, 2025

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Save 100% on your flight
per person
Aug 18 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
9.2/10 Wonderful! (1,003 reviews)
A great property and great activity to do around the hotel

Reviewed on Jun 9, 2025

Falmouth Tides

Falmouth Tides

2.5 out of 5
Falmouth Heights
Save 100% on your flight
per person
Aug 19 - Aug 23
found 15 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
9.2/10 Wonderful! (572 reviews)
Great hotel with super friendly and helpful staff. The location is perfect—close to everything and easy to get around. Highly recommend!

Reviewed on Jun 11, 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

Red Roof Inn PLUS+ West Springfield
Red Roof Inn PLUS+ West Springfield
2.5 out of 5
1254 Riverdale Street, West Springfield, MA
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $102 total per night from Jun 25 to Jun 26
$102 total
Jun 25 - Jun 26
Total includes taxes and fees
6.8/10 (1,001 reviews)
"Amazing space clean and well maintained"

Reviewed on Jun 10, 2025

Red Roof Inn PLUS+ West Springfield
D. Hotel Suites & Spa
D. Hotel Suites & Spa
3 out of 5
1 Country Club Rd, Holyoke, MA
$150 nightly
The price is $168 total per night from Jun 22 to Jun 23
$168 total
Jun 22 - Jun 23
Total includes taxes and fees
9.2/10 Wonderful! (2,268 reviews)
"It was the perfect stay for our family for a night! It was so clean, everyone was kind, the breakfast was AMAZING & so was the indoor pool! Highly recommend!"

Reviewed on Jun 15, 2025

D. Hotel Suites & Spa
Quality Inn West Springfield
Quality Inn West Springfield
2.5 out of 5
1150 Riverdale St, West Springfield, MA
$89 nightly
The price is $102 total per night from Jun 29 to Jun 30
$102 total
Jun 29 - Jun 30
Total includes taxes and fees
7/10 Good! (1,005 reviews)
"Comfort able and breakfast are good"

Reviewed on Jun 13, 2025

Quality Inn West Springfield
See all 463 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 $696 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.