Chesterfield Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Chesterfield Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Ready to book your vacation to Chesterfield?
Chesterfield Hotel Deals
Chesterfield Hotel by OYO Hwy 9
321 East Blvd Chesterfield SC
Fully refundableReserve now, pay when you stay
CA $80
CA $92 total
Oct 13 - Oct 14
includes taxes & fees
4/10 (14 reviews)
"They need to remove all of the trash from the outside. And get the cigarette smell from the rooms"
Reviewed on Oct 5, 2026
12 Acre Pond House in Chesterfield - come fish and paddle board! 2BR 2B
Chesterfield SC
CA $271
CA $424 total
Oct 29 - Oct 30
includes taxes & fees
10/10 Exceptional! (5 reviews)
"We had a fun time during our 2 night stay. We caught almost 10 fish (catfish, blue gills, etc). The property is clean and spacious. Kitchen and bath are welcoming. Our host was quick to answer any questions we had. The check-in process was very simple,and our dogs loved it too!"
Reviewed on Sep 28, 2026
2 Full Beds Non-Smoking
Chesterfield, SC SC
Fully refundable
CA $92
CA $113 total
Oct 13 - Oct 14
includes taxes & fees
10/10 Exceptional! (168 reviews)
A reliable option with essential comforts that satisfied our requirements withou ...
"A reliable option with essential comforts that satisfied our requirements without stressing over little details too much."
Reviewed on Jun 12, 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.
Frequently asked questions
How much does a Chesterfield vacation package cost?
You'll find cheap prices from CA $911 on Expedia for your Chesterfield getaway. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Chesterfield costs.
What are the cheapest months to go to Chesterfield?
January, February and July are great times to look for cheap Chesterfield vacation packages. Opting to travel in quieter months means you can generally find better prices on flights and hotels.
How many days is enough for Chesterfield?
With a well-organized schedule, you can easily visit the top Chesterfield attractions in a handful of days. But if you'd like to discover hidden spots or go on day trips, consider booking your Chesterfield vacation for longer.
How to find the best Chesterfield package deals?
Use Expedia's filter tool to find some terrific Chesterfield package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or search for Chesterfield package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Chesterfield vacation as a package?
You can enjoy significant savings on your next Chesterfield break by booking a personalized vacation package. Check the "Package" heading, then enter your travel dates and destination to browse the best flight 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're considering a spur-of-the-moment Chesterfield getaway, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find sensational deals on your hotels and flights by booking well in advance.
How to plan a trip to Chesterfield?
- Pick your travel dates: The things you'd like to do in Chesterfield and your favourite season will help you decide when to get away.
- Plan your budget wisely: As well as the cost of your hotel, you should factor in other expenses too. These include transportation, food and flights. Also, set aside some extra funds for unexpected expenses that may arise during your trip to Chesterfield.
- Determine how many days away: Start by listing all the sights and activities you'd like to experience in Chesterfield. Then, estimate how long you'll need at each, along with any travel time.
- Combine your airfare and accommodations: Once you've nailed down your travel dates and duration, lock in the right Chesterfield vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
