Chesterfield Vacations from $494
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 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
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.
The Latest Chesterfield vacation packages
Price found within the past 48 hours. Click for updated prices.
Wedmore Place
$537
per person
Nov 24 - Nov 27
found 1 day ago
Roundtrip flight included
New York (NYC) to Richmond (RIC)
9.4/10 Exceptional! (1,008 reviews)
It’s located in a very nice winery, calm and beautiful!
The breakfast lacks better coffee, fresh baked bread, needs fresh eggs not fake eggs etc…
Reviewed on Aug 30, 2026
Don't see what you're looking for?
See all available trips from Columbus to Chesterfield
View all tripsStay 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 Center 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.
Civilian Conservation Corps Museum
This intimate museum chronicles the young men who built Virginia's parks during the Great Depression. Explore historical artifacts and photographs while surrounded by the natural beauty they helped preserve.
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.
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
Richmond: Guided Hike in James River Park
$35
per adult
100% of travellers recommend
Downtown Richmond Must-See Landmarks with Self-Guided Audio Tour
$11
per traveler
80% of travellers recommend
Chesterfield Hotel Deals
Omni Richmond Hotel
100 S 12th St Richmond VA
Fully refundableReserve now, pay when you stay
$167 nightly
$194 total
Sep 7 - Sep 8
Total with taxes and fees
The Jefferson Hotel
101 West Franklin Street Richmond VA
Fully refundableReserve now, pay when you stay
$295 nightly
$343 total
Sep 7 - Sep 8
Total with taxes and fees
9.8/10 Exceptional! (1,005 reviews)
"This is a first rate hotel with superb staff and facilities, including an excellent restaurant on site. Great location in downtown Richmond."
Reviewed on Aug 31, 2026
Graduate by Hilton Richmond
301 West Franklin Street Richmond VA
Fully refundableReserve now, pay when you stay
$147 nightly
$171 total
Sep 8 - Sep 9
Total with taxes and 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.
Find the Best Chesterfield Vacation Packages
Chesterfield Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Richmond Intl. Airport (RIC) |
Population | 3,800 |
Max Temp Winter | 50ºF |
Max Temp Summer | 90ºF |
Top Sights | Pocahontas State Park, Uptown Alley and Pocahontas State Park Museum |
More vacations you might like
Frequently asked questions
How much does a Chesterfield vacation package cost?
You can snap up a vacation package to this popular destination from $494 on Expedia. However, how much your vacation to Chesterfield costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Chesterfield?
If you're looking to snag a cheap Chesterfield vacation package, consider visiting in February, November and December. You'll generally find better rates on airfares and hotels during these months — perfect for a budget-friendly getaway.
How many days is enough for Chesterfield?
Usually, a handful of days is enough to tick off the main attractions during your Chesterfield vacation. But if you want to have time to unwind or go on day trips, consider extending your itinerary.
Is it worth booking a vacation package to Chesterfield?
From attractions such as Castlewood and Magnolia Grange to its terrific history, a Chesterfield vacation is sure to exceed your expectations. With so much to see and do, it's time to find out for yourself why Chesterfield is such a good vacation 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 vacation as a package?
An Expedia vacation 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 vacation 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 vacation.
How to plan a trip to Chesterfield?
- Choose the ideal time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to Chesterfield.
- Budget wisely: As well as the price of your accommodations, you'll need to consider other expenses too. These include food, flights and transportation. Also, put aside a little extra for unexpected expenses that may come up during your trip to Chesterfield.
- Explore Chesterfield using our trip planning tool: Gain insights into the top attractions and best hotels for your trip to Chesterfield. You can also save your must-visit places, collaborate with friends and family and organize your plans in one place.
- Determine how many days away: Start by making a list of all the activities and sights you'd like to get to in Chesterfield. Then, estimate how long you'll need at each, along with any travel time.
- Bundle your airfare and accommodations: Once you've nailed down your trip dates and duration, book the right Chesterfield vacation package for you.
- Book any excursions or activities: Now to the fun part — organizing everything you want to do and see. Check out some of the top things to do in Chesterfield in Chesterfield and book your tickets early to save time (and maybe some dollars too!).
Does Expedia offer Book Now, Pay Later Chesterfield vacation packages?
If you're anything like us, you love traveling the world but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the overall cost of your Chesterfield break across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure great vacation packages with payment plans as soon as you see them.
Explore a world of travel with Expedia
- Downtown Richmond Hotels
- Richmond Hotels
- Cheap Hotels in Richmond
- Petersburg Hotels
- All-Inclusive Resorts in Virginia
- Cabin Rentals in Virginia
- Williamsburg Hotels
- Virginia Hotels
- Hotels near Short Pump Town Center
- Hotels near Greater Richmond Convention Center
- Midlothian Hotels
- Chesterfield Hotels
- Motels in Richmond
- Hotels near Richmond Intl.
- Pet-Friendly Hotels in Richmond
- Chester Hotels
- Resorts & Hotels with Spas in Virginia
- Marriott Hotels & Resorts in Bermuda
- Colonial Heights Hotels
- Flights to Chesterfield
- Flights from Chesterfield
- Flights from Richmond Intl.
- Flights from Houston (IAH) to Richmond (RIC)
- Flights from Minneapolis (MSP) to Richmond (RIC)
- Flights from Nashville (BNA) to Richmond (RIC)
- Flights to Richmond
- Flights to Virginia
- Flights from Providence (PVD) to Richmond (RIC)
- Flights from Seattle (SEA) to Richmond (RIC)
- Flights from Jacksonville (JAX) to Richmond (RIC)
- Flights from Salt Lake City (SLC) to Richmond (RIC)
- Flights from Pittsburgh (PIT) to Richmond (RIC)
- Flights from Tampa (TPA) to Richmond (RIC)
- Flights from New York (LGA) to Richmond (RIC)
- Flights from Detroit (DTW) to Richmond (RIC)
- Flights from San Francisco (SFO) to Richmond (RIC)
- Flights from Indianapolis (IND) to Richmond (RIC)
- Flights from Miami (MIA) to Richmond (RIC)
- Flights from Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
- Flights from Atlanta (ATL) to Richmond (RIC)
- Flights from Los Angeles (LAX) to Richmond (RIC)
- Flights from New York (JFK) to Richmond (RIC)
- Flights from Charlotte (CLT) to Richmond (RIC)
- Flights from Denver (DEN) to Richmond (RIC)
- Flights from San Juan (SJU) to Richmond (RIC)
- Flights from Phoenix (PHX) to Richmond (RIC)
- Flights from Fort Lauderdale (FLL) to Richmond (RIC)
- Flights from Las Vegas (LAS) to Richmond (RIC)
- Flights from Austin (AUS) to Richmond (RIC)
- Flights from Charleston (CHS) to Richmond (RIC)
- Flights from Philadelphia (PHL) to Richmond (RIC)
- Flights from Raleigh (RDU) to Richmond (RIC)
- Flights from Chicago (ORD) to Richmond (RIC)
- Flights from Orlando (MCO) to Richmond (RIC)
- Flights from San Diego (SAN) to Richmond (RIC)
- Flights from Boston (BOS) to Richmond (RIC)
- Flights from Hartford (BDL) to Richmond (RIC)
- Flights from Dallas (DFW) to Richmond (RIC)
- Virginia State Capitol
- Chippenham Hospital
- Henricus Historical Park
- Broad Street
- The Lazy Daisy
- Richmond National Battlefield Park
- Castlewood
- Canal Walk
- Virginia State University
- Chesterfield Towne Center
- Visit Virginia
- Shirley Plantation
- Maymont Park
- Hunter Holmes McGuire VA Medical Center
- Pocahontas State Park
- Keystone Antique Truck and Tractor Museum
- Richmond Vacations
- Parker's Battery Park
- Virginia Museum of Fine Arts
- Libby Hill Park
- Virginia Vacations
- Johnston-Willis Hospital
- Visit Downtown Richmond
- Putt-Putt Fun Center
- Hollywood Cemetery
- Southpark Mall
- Magnolia Grange
- Iron Bridge Sports Park
- Virginia Commonwealth University
- Swaders Sports Park
- Greater Richmond Convention Center
- College of William and Mary
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
