Chesterfield Vacations from $340

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, 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.
Holiday Inn Club Vacations Williamsburg Resort by IHG

Holiday Inn Club Vacations Williamsburg Resort by IHG

3.5 out of 5
Save 100% on your flight
Price was $515, price is now $340 per person
$340
per person
Jan 25 - Jan 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
18/10 Exceptional! (525 reviews)
Everything was wonderful, it was clean and communication was great

Reviewed on Nov 23, 2025

The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Save 100% on your flight
Price was $1,055, price is now $703 per person
$703
per person
Dec 28 - Jan 4
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
17.6/10 Exceptional! (1,314 reviews)
Nice, clean room, The staff is amazing. The valet team is wonderful. The bar/restaurant staff is great. All-around excellent experience. I would definitely book this hotel again.

Reviewed on Nov 20, 2025

The Berkeley Hotel

The Berkeley Hotel

4 out of 5
Downtown Richmond
Price was $936, price is now $631 per person
$631
per person
Dec 28 - Jan 4
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
17.6/10 Exceptional! (1,540 reviews)
Room was beautiful. Bed and pillows were 5 star. Hotel was under construction, so it was very noisy. Had to schedule maid service multiple times before they would actually do it. Room had no table or chairs so it was difficult to eat in the room.

Reviewed on Nov 17, 2025

Graduate by Hilton Richmond

Graduate by Hilton Richmond

4 out of 5
Downtown Richmond
Price was $998, price is now $721 per person
$721
per person
Dec 28 - Jan 4
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
16.8/10 Exceptional! (1,395 reviews)
Very courteous front desk. Check in was quick and easy.

Reviewed on Nov 21, 2025

A house full of steel balls and games

A house full of steel balls and games

2.5 out of 5
Dumbarton
Price was $649, price is now $474 per person
$474
per person
Dec 28 - Jan 4
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
19.2/10 Exceptional! (99 reviews)
The room is amazing! The bed is more comfortable than my own at home! Host is amazing! Amazing games and a great space! I Can't wait to recommend to friends!

Reviewed on Nov 8, 2025

Don't see what you're looking for?
See all available trips from Columbus to Chesterfield
View all trips

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now

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

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

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

Pocahontas State Park Museum

You can spend an afternoon browsing the exhibits at Pocahontas State Park Museum in Chesterfield. Take in the live music in this family-friendly area.

Pocahontas State Park Museum

What to do in Chesterfield

Historic Trolley Tour

Historic Trolley Tour

$42
per adult
100% of travellers recommend
Historic Trolley Tour
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
See all activities in Chesterfield

Chesterfield Hotel Deals

The Jefferson Hotel

The Jefferson Hotel

5 out of 5
101 West Franklin Street Richmond VA
Fully refundableReserve now, pay when you stay
$305 nightly
The price is $355 total per night from Nov 30 to Dec 1
$355 total
Nov 30 - Dec 1
Total with taxes and fees
9.8/10 Exceptional! (1,006 reviews)
Amazing place - phenomenal staff. Clearly made us feel like royalty. Will absolutely return!

Reviewed on Nov 17, 2025

The Jefferson Hotel
Omni Richmond Hotel

Omni Richmond Hotel

4 out of 5
100 S 12th St Richmond VA
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $176 total per night from Dec 7 to Dec 8
$176 total
Dec 7 - Dec 8
Total with taxes and fees
9/10 Wonderful! (1,249 reviews)
Check in staff was excellent

Reviewed on Nov 20, 2025

Omni Richmond Hotel
Drury Plaza Hotel Richmond

Drury Plaza Hotel Richmond

3 out of 5
11049 West Broad St Glen Allen VA
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $128 total per night from Nov 30 to Dec 1
$128 total
Nov 30 - Dec 1
Total with taxes and fees
9.6/10 Exceptional! (2,822 reviews)
The room was great and was as pictured online with no surprises and very clean. Both the dinner and breakfast buffet were excellent

Reviewed on Nov 22, 2025

Drury Plaza Hotel Richmond
See all 945 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Chesterfield vacation package cost?
You can snap up a vacation package to this popular destination from $340 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.

Explore a world of travel with Expedia

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