Chesterfield Vacations from $413

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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.

The Latest Chesterfield vacation packages

Price found within the past 48 hours. Click for updated prices.
Vacation Village At Williamsburg

Vacation Village At Williamsburg

3 out of 5
Save 100% on your flight
per person
Aug 18 - Aug 23
found 3 hours ago
Roundtrip flight included
New York (JFK) to Richmond (RIC)
8.8/10 Excellent! (1,459 reviews)
Old but clean . Great for a family vacation

Reviewed on Jun 30, 2025

Westgate Historic Williamsburg Resort

Westgate Historic Williamsburg Resort

3.5 out of 5
Save 100% on your flight
per person
Aug 18 - Aug 23
found 3 hours ago
Roundtrip flight included
New York (JFK) to Richmond (RIC)
8.4/10 Very Good! (1,006 reviews)
Not sure if it's all doors, but my door's lock

Reviewed on Jun 29, 2025

The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Save 100% on your flight
per person
Aug 20 - Aug 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
9/10 Wonderful! (1,247 reviews)
The rooms! Hands down the best room I've ever stayed in given the price.

Reviewed on Jun 30, 2025

Barsala At Sphere Apartments

Barsala At Sphere Apartments

3.5 out of 5
Save 100% on your flight
per person
Aug 20 - Aug 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
9/10 Wonderful! (12 reviews)
This was a clean, well-equipped and comfortable apartment. The location is good but does require a car to explore the city and pick up groceries. Parking was easy and free. The balcony was a nice place to sit as the temperature got warmer. Air conditioning was very effective. Would stay again.

Reviewed on Apr 24, 2025

Linden Row Inn

Linden Row Inn

3 out of 5
Downtown Richmond
Save 100% on your flight
per person
Sep 25 - Sep 28
found 24 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
9.2/10 Wonderful! (1,060 reviews)
Everything related to the hotel was awesome. Very old and charming building, I could stay there for years. No laundry or parking on site though. Only thing that was irritating was panhandling in the area, not that it’s the hotel’s fault.

Reviewed on Jun 25, 2025

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Discover the most popular places to visit in Chesterfield

While hiking with my wife in Pocahontas State Park in Virginia we came across this doll left on the trail. I thought it would make for a cool photo.

Pocahontas State Park

4/5(29 reviews)

You can take time to visit Pocahontas State Park during your travels to Chesterfield. Attend a sporting event in this family-friendly area.

Pocahontas State Park

Castlewood

4/5(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.

Castlewood

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.

Magnolia Grange

What to do in Chesterfield

Historic Trolley Tour

Historic Trolley Tour

$42
per adult
Historic Trolley Tour
Richmond: Guided Hike in James River Park

Richmond: Guided Hike in James River Park

$29
per adult
Richmond: Guided Hike in James River Park
Ascending the Capitol Steps

Haunted Capitol Hill Ghost Tour

$27
per adult
100% of travellers recommend
Haunted Capitol Hill Ghost Tour
See all activities in Chesterfield

Chesterfield Hotel Deals

Studio 6 Richmond, VA - Airport
Studio 6 Richmond, VA - Airport
2 out of 5
580 Trampton Road, Sandston, VA
Fully refundableReserve now, pay when you stay
$70 nightly
The price is $82 total per night from Jul 20 to Jul 21
$82 total
Jul 20 - Jul 21
Total includes taxes and fees
9/10 Wonderful! (116 reviews)
"We were very pleased with our stay in all aspects! This is a hidden gem of a quality hotel and a great value. Highly recommend and we will definitely be back!"

Reviewed on Jun 30, 2025

Studio 6 Richmond, VA - Airport
Omni Richmond Hotel
Omni Richmond Hotel
4 out of 5
100 S 12th St, Richmond, VA
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $185 total per night from Jul 20 to Jul 21
$185 total
Jul 20 - Jul 21
Total includes taxes and fees
8.8/10 Excellent! (1,130 reviews)
"Nice hotel."

Reviewed on Jun 26, 2025

Omni Richmond Hotel
Regency Inn Richmond
Regency Inn Richmond
2 out of 5
1500 Eastridge Road, Richmond, VA
Fully refundableReserve now, pay when you stay
$67 nightly
The price is $78 total per night from Jul 14 to Jul 15
$78 total
Jul 14 - Jul 15
Total includes taxes and fees
7/10 Good! (1,009 reviews)
"Peace and quiet very friendly staff that makes you feel like home 😊 and the only thing that I didn’t like about my stay was no internet and power goes off a lot"

Reviewed on Jun 25, 2025

Regency Inn Richmond
See all 963 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.

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

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Frequently asked questions

How much does a Chesterfield vacation package cost?
You can snap up a vacation package to this popular destination from $413 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. Bundle your airfare and accommodations: Once you've nailed down your trip dates and duration, book the right Chesterfield vacation package for you.
  6. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.