Chesterfield Vacations from $352

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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.
Best Western Plus Governor's Inn

Best Western Plus Governor's Inn

2.5 out of 5
Bon Air
Price was $459, price is now $352 per person
$352
per person
Jul 3 - Jul 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
8.4/10 Very Good! (1,000 reviews)
Very friendly staff. Good breakfast but wish didn't end so early. Parking was easy except Saturday evening. Love the brick exterior! Felt safe. Every hotel needs to dust better above beds, mirrors, back splashes, lights.

Reviewed on May 15, 2026

The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was $596, price is now $457 per person
$457
per person
Jul 7 - Jul 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
8.8/10 Excellent! (1,356 reviews)
Breakfast was very good. But there was only one very capable waitress serving both those eating in and carry out orders.

Reviewed on May 18, 2026

Hilton Richmond Downtown

Hilton Richmond Downtown

4 out of 5
Downtown Richmond
Price was $628, price is now $499 per person
$499
per person
Jul 7 - Jul 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
8.2/10 Very Good! (1,000 reviews)
Breakfast was delicious, the rooms were clean, the beds were extremely comfortable, the we really enjoyed the restaurant for a light meal

Reviewed on May 17, 2026

Wingate by Wyndham Richmond Short Pump

Wingate by Wyndham Richmond Short Pump

3 out of 5
Short Pump
Price was $546, price is now $440 per person
$440
per person
Jul 7 - Jul 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
8.4/10 Very Good! (1,845 reviews)
There was a hot breakfast available every day as well as other choices. Most of the staff were great.

Reviewed on May 19, 2026

The Virginia Cliffe Inn

The Virginia Cliffe Inn

2.5 out of 5
Price was $670, price is now $544 per person
$544
per person
Jun 23 - Jun 26
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
9.6/10 Exceptional! (131 reviews)
There is a train nearby and you can hear the train pretty often. We didn't mind, but I think it's worth mentioning since it was pretty loud and pretty often.

Reviewed on Apr 19, 2026

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Discover the most popular places to visit in Chesterfield

Richmond_PocahontasStatePark_553248621532661487_04

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

Richmond: Guided Hike in James River Park

Richmond: Guided Hike in James River Park

$35
per adult
100% of travellers recommend
Richmond: Guided Hike in James River Park
A bus tour of Richmond’s most unusual, unexpected, and humorous stories — history with a twist!

Offbeat History Tour of Richmond on a bus

$45
per adult
Offbeat History Tour of Richmond on a bus
Richmond Ghost Tour: Sinister Secrets of Shockoe Bottom

Richmond Ghost Tour: Sinister Secrets of Shockoe Bottom

$26
per adult
90% of travellers recommend
Richmond Ghost Tour: Sinister Secrets of Shockoe Bottom
See all activities in Chesterfield

Chesterfield Hotel Deals

Studio 6 Richmond Airport

Studio 6 Richmond Airport

2 out of 5
580 Trampton Road Sandston VA
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $103 total per night from May 31 to Jun 1
$103 total
May 31 - Jun 1
Total with taxes and fees
8.4/10 Very Good! (696 reviews)
"The room was dirty. The wall behind the bed had dirty hand prints. Overall the place felt dirty."

Reviewed on May 20, 2026

Studio 6 Richmond Airport
Graduate by Hilton Richmond

Graduate by Hilton Richmond

4 out of 5
301 West Franklin Street Richmond VA
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $169 total per night from Jun 10 to Jun 11
$169 total
Jun 10 - Jun 11
Total with taxes and fees
8.4/10 Very Good! (1,365 reviews)
"Super good service from the first valet to the last front desk agent who checked us out. The suite was huge and ideal for a family with children as there was a bunk bed in the living room. WiFi and TV were both excellent and we felt very much at home."

Reviewed on May 20, 2026

Graduate by Hilton Richmond
Omni Richmond Hotel

Omni Richmond Hotel

4 out of 5
100 S 12th St Richmond VA
Fully refundableReserve now, pay when you stay
$175 nightly
The price is $204 total per night from May 31 to Jun 1
$204 total
May 31 - Jun 1
Total with taxes and fees
9/10 Wonderful! (1,430 reviews)
"Front desk was not very courteous"

Reviewed on May 20, 2026

Omni Richmond Hotel
See all 1,072 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 $352 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.