Chesterfield Vacations

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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.

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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
$113 nightly
The price is $126 total per night from Sep 28 to Sep 29
$126 total
Sep 28 - Sep 29
Total with taxes and fees
8.8/10 Excellent! (646 reviews)
"Excellent location. Friendly staff."

Reviewed on Sep 17, 2025

Berkshire Mountain Lodge
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 Oct 1 to Oct 2
$102 total
Oct 1 - Oct 2
Total with taxes and fees
6.8/10 (1,013 reviews)
"Excellent overall!"

Reviewed on Sep 13, 2025

Red Roof Inn PLUS+ West Springfield
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
$99 nightly
The price is $113 total per night from Oct 2 to Oct 3
$113 total
Oct 2 - Oct 3
Total with taxes and fees
7/10 Good! (1,028 reviews)
"Convenient nice cozy hotel with breakfast included and spacious rooms."

Reviewed on Sep 23, 2025

Quality Inn West Springfield
See all 472 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.

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Frequently asked questions

How much does a Chesterfield vacation package cost?
You'll find cheap prices 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.