Chesterfield Vacations from $673
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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.
Four Seasons Hotel Boston
Bay Village
$1,236
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
9.4/10 Exceptional! (487 reviews)
Your staff is Five star! Hotel needs updating badly. My far the worst Four Seasons we have stayed in.
On the day of check-in, our flight was delayed and we got in at 2:30 in the morning had room service and it was an edible. Your staff indicated they would remove the charges, but I see we were still charged for them as well.
Reviewed on Oct 6, 2026
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View all tripsStay 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.
Chesterfield Gorge Reservation
You can take time to visit Chesterfield Gorge Reservation during your travels to Chesterfield. Amble around the area's parks or visit its shops.
Chesterfield Town Hall
After visiting Chesterfield Town Hall, make a plan to see the other sights and activities in Chesterfield. Amble around the area's parks or visit its shops.
Chesterfield Public Library
Chesterfield Public Library is just one of the places to see in Chesterfield, so why not enjoy the other things to explore during your travels? Amble around the area's parks or visit its shops.
Oak Hill
Commune with nature and explore the great outdoors at Oak Hill during your travels in Chesterfield. Amble around the area's parks or visit its shops.
Krug Sugarbush
You can take time to visit Krug Sugarbush during your travels to Chesterfield. Amble around the area's parks or visit its shops.
Chesterfield Hotel Deals
Quality Inn West Springfield
1150 Riverdale St West Springfield MA
Fully refundable
$89 nightly
$101 total
Nov 8 - Nov 9
Total with taxes and fees
7.2/10 Good! (1,006 reviews)
"Property is dated. Balconies dirty with spiders. Room cleaning spotty. Breakfast weak. Same food each day. Only stayed here as daughter was in ICU."
Reviewed on Oct 14, 2026
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
$142 nightly
$158 total
Oct 26 - Oct 27
Total with taxes and fees
9.2/10 Wonderful! (2,092 reviews)
"We loved our stay. The housekeeping and amenities were too notch. Perfect family-friendly hotel near the Yankee Candle Factory."
Reviewed on Oct 13, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
$125 nightly
$139 total
Nov 3 - Nov 4
Total with taxes and fees
9/10 Wonderful! (1,206 reviews)
"Beautiful location. Easy access to local restaurants and hiking trails."
Reviewed on Oct 14, 2026
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 $673 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.
