Chesterfield Holidays
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Top hotels in Chesterfield
The Jefferson Hotel
101 West Franklin Street Richmond VA
Fully refundableReserve now, pay when you stay
S$421
30 Aug - 31 Aug
includes taxes & fees
9.8/10 Exceptional! (1,006 reviews)
"Really enjoyed our weekend at the Jefferson leaving the hotel only once. Got massages, a pedicure, swam and relaxed in the salt water pool and outdoor deck and ate all our meals at their Lemaire restaurant. The hotel is beautiful with quite a history. Our room was very spacious with spacious bathroom ..."
Reviewed on 10 Aug, 2026
Omni Richmond Hotel
100 S 12th St Richmond VA
Fully refundableReserve now, pay when you stay
S$266
16 Aug - 17 Aug
includes taxes & fees
9/10 Wonderful! (1,532 reviews)
"Clean quiet room. Good water pressure in shower. Lush bathrobe. Slept very well. Enjoyed free coffee in morning."
Reviewed on 10 Aug, 2026
Graduate by Hilton Richmond
301 West Franklin Street Richmond VA
Fully refundableReserve now, pay when you stay
S$206
16 Aug - 17 Aug
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)
Virginia's largest state park offers 90+ miles of trails through lush forests and three serene lakes. Explore world-class mountain biking routes or cool off at the seasonal Aquatic Centre after a day of adventure.
Castlewood
8.0/10 (1 review)
This distinctive Federal-style house (1817) features a rare five-part architectural layout. Explore its well-preserved interior while learning about 19th-century Chesterfield County life through curated exhibits.
Chesterfield Historical Society of Virginia
The Chesterfield Historical Society preserves 400 years of local heritage through its museum complex and historic sites. Explore exhibits on Native American culture, colonial settlements, and wartime history.
Civilian Conservation Corps Museum
This intimate museum chronicles the young men who built Virginia's parks during the Great Depression. Explore historical artefacts and photographs while surrounded by the natural beauty they helped preserve.
Magnolia Grange
This Federal-style plantation home from 1822 showcases elaborate ceiling medallions and carved details. Explore elegantly restored rooms with period antiques while docents reveal the stories of past residents.
What to do in Chesterfield
Downtown Richmond Must-See Landmarks with Self-Guided Audio Tour
S$13
per traveller
80% of travellers recommend
Frequently asked questions
How much does a Chesterfield holiday package cost?
You can snap up a holiday package to this popular destination on Expedia. However, how much your holiday to Chesterfield costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Chesterfield?
Plan your getaway for the low season and you're likely to find cheap Chesterfield holiday packages. Bear in mind that school holiday periods and major local events can impact prices, so do a little research before booking.
How many days is enough for Chesterfield?
Generally, a handful of days is enough to visit the main attractions during your Chesterfield holiday. However, if you prefer to have some time to kick back or go on day trips, think about extending your itinerary.
Is it worth booking a holiday package to Chesterfield?
From cool attractions such as Castlewood and Magnolia Grange to its epic history, a Chesterfield holiday guarantees an unforgettable adventure. With so much to do and see, find out for yourself why Chesterfield is such a good holiday destination.
How to find the best Chesterfield package deals?
Begin your search for a Chesterfield package deal by entering your destination and preferred trip dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Chesterfield package deal right away, just change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Chesterfield getaway off to a flying start.
Is it cheaper to book a Chesterfield holiday as a package?
An Expedia holiday package could land you great savings when compared to booking flights and stays individually. Better still, you can tailor your Chesterfield getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a holiday package to Chesterfield?
Secure incredible bargains by booking your flights ahead of time with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for an impromptu Chesterfield holiday.
How to plan a trip to Chesterfield?
- Pick your travel dates: What you'd like to do in Chesterfield and your preferred season will help you decide when to go.
- Set your budget: Factor in costs like flights, meals and transportation when calculating how much to set aside for your trip to Chesterfield. Then, pick a hotel that matches your budget, whether that's an economical stay or a high-end getaway.
- Decide how long to go for: Now that you know more about Chesterfield, you can figure out the right length of your holiday. Put together a draft itinerary and allocate enough time to get through everything on your must-do list.
- Bundle your airfare and accommodation: Once you've nailed down your trip dates and duration, lock in the right Chesterfield holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
