Chesterfield Vacation Packages
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Your Chesterfield Vacation
Lock in a Chesterfield vacation package that includes everything you need and no unnecessary extras. Great for nightlife, cafes and festivals, think about basing yourself in the neighborhood of Downtown Richmond. A trip to Chesterfield is a wonderful opportunity to see the sights. Be sure to stop by big-name attractions such as Pocahontas State Park, Castlewood and Magnolia Grange. Expedia has what you need to escape your daily routine. Tailor your vacation to Chesterfield to suit your style of travel, whatever that may look like.
Top Chesterfield Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Commonwealth
Downtown Richmond
CA $1,272
per person
Dec 17 - Dec 22
found 20 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Richmond (RIC)
8.8/10 Excellent! (1,407 reviews)
Water pressure in the shower was low. The sink drained very slowly. Other than that everything was great.
Reviewed on Oct 15, 2026
Kingsmill Resort
Kingsmill
CA $1,370
per person
Dec 5 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.6/10 Excellent! (1,006 reviews)
Room was big (one bedroom condo) and clean. However, it needs more proper maintenance. Some lights (lamp, overhead) were burned out and have not been replaced. The toilet is not properly attached to the floor (it moves when you sit).
Reviewed on Oct 14, 2026
Ready to book your vacation to Chesterfield?
Chesterfield Hotel Deals
Holiday Inn & Suites Richmond West End
8008 W. Broad St Richmond VA
Fully refundable
CA $146
CA $170 total
Nov 15 - Nov 16
includes taxes & fees
Comfort Suites At Virginia Center Commons
10601 Telegraph Rd Glen Allen VA
Fully refundable
CA $120
CA $140 total
Oct 25 - Oct 26
includes taxes & fees
8.2/10 Very good! (1,652 reviews)
"Everything was great. Clean, comfortable, and friendly and helpful staff. Breakfast was good with eggs (fried and scrambled), sausage (links and patties), bagels and toast, cereals, juice, etc. Had an indoor heated pool and hot tub were clean and maintained. Room was great. Very clean and comfortable. ..."
Reviewed on Oct 15, 2026
The Jefferson Hotel
101 West Franklin Street Richmond VA
Fully refundableReserve now, pay when you stay
CA $448
CA $521 total
Nov 10 - Nov 11
includes taxes & fees
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.
Stay near popular Chesterfield attractions
Pocahontas State Park
8.4/10 (31 reviews)
You can take time to visit Pocahontas State Park during your travels to Chesterfield. Attend a sporting event in this family-friendly area.
Castlewood
8.0/10 (1 review)
You can find out about the history of Chesterfield Court House with a stop at Castlewood. Stroll along the riverfront or attend a sporting event in the area.
Civilian Conservation Corps Museum
You can spend an afternoon browsing the exhibits at Civilian Conservation Corps Museum in Chesterfield. Take in the live music in this family-friendly area.
Magnolia Grange
You can browse the exhibits at Magnolia Grange, a museum with a storied past, during your travels to Chesterfield Court House. Amble around the area's riverfront or attend a sporting event.
Chesterfield Historical Society of Virginia
You can learn about the history of Chesterfield Court House with a visit to Chesterfield Historical Society of Virginia. Stroll along the riverfront or attend a sporting event in the area.
What to do in Chesterfield
Richmond: Guided Hike in James River Park
CA $49
per adult
100% of travellers recommend
Downtown Richmond Must-See Landmarks with Self-Guided Audio Tour
CA $14
per traveller
80% of travellers recommend
Richmond Ghost Tour: Sinister Secrets of Shockoe Bottom
CA $36
per adult
90% of travellers recommend
Frequently asked questions
How much does a Chesterfield vacation package cost?
You can pick up a vacation package to this destination from CA $1,004 on Expedia. However, how much your vacation to Chesterfield costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Chesterfield?
Plan your getaway for the off-season and you're likely to find cheap Chesterfield vacation packages. Remember that public holidays and major local events can have an impact on prices, so do a little research before booking.
How many days is enough for Chesterfield?
With a well-organized schedule, you can easily visit the main Chesterfield sights in a handful of days. But if you prefer to discover lesser-known spots or go on day tours, consider booking your Chesterfield vacation for longer.
Is it worth booking a vacation package to Chesterfield?
Boasting a host of highlights starting with its top-notch history, Chesterfield is a good vacation destination. Whether you'd like to check out attractions like Castlewood and Magnolia Grange or venture off the beaten track, you'll find plenty to see and do on your Chesterfield vacation.
How to find the best Chesterfield package deals?
Use Expedia's filter tool to help you find some of the best Chesterfield package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for Chesterfield package deals in the off-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 well in advance.
Is it cheaper to book a Chesterfield vacation as a package?
You can enjoy significant savings on your Chesterfield getaway by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to view some great flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Chesterfield?
Enjoy incredible bargains by reserving your flights ahead of time with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Chesterfield escape.
How to plan a trip to Chesterfield?
- Choose when to get away: Check your calendar and get your bags packed. Your preferred time of year and the type of activities available will also help you decide when to vacation in Chesterfield.
- Set your budget: Consider expenses like flights, food and transportation when working out how much to save for your trip to Chesterfield. Then, select a property that suits your budget, whether that's a wallet-friendly option or a lavish retreat.
- Decide how long to go away for: Now that you're up to speed on Chesterfield, you can work out the perfect length of your vacation. Create a rough itinerary and allocate enough time to cover everything you want to do.
- Combine your airfare and accommodations: After you've nailed down your trip dates and duration, lock in the ideal 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.
