Chesterfield Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥109,000 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

Find the Best Chesterfield Vacation Packages

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
The price is ￥47,696 per night from Jul 19 to Jul 20
￥47,696
￥55,462 total
Jul 19 - Jul 20
includes taxes & fees
9.8/10 Exceptional! (1,009 reviews)
"Beautiful hotel , lovely large rooms & the most comfortable bed! Actually looked up the pillow brand, because they were the most comfortable pillows I’ve slept on ."

Reviewed on Jul 11, 2026

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
The price is ￥28,942 per night from Jul 19 to Jul 20
￥28,942
￥33,655 total
Jul 19 - Jul 20
includes taxes & fees
9/10 Wonderful! (1,492 reviews)
"The room...we upgraded to a superior room ...was very noisy...like no insulation...you could plainly hear people in other rooms talking....NO wifi...you have to PAY...no parking...you have to PAY 35 bucks every day...and no free breakfast....you have to pay for everything and the staff was not helpful....never ..."

Reviewed on Jul 11, 2026

Omni Richmond Hotel
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
The price is ￥22,406 per night from Aug 5 to Aug 6
￥22,406
￥26,054 total
Aug 5 - Aug 6
includes taxes & fees
8.4/10 Very Good! (1,415 reviews)
"Thank you!"

Reviewed on Jul 11, 2026

Graduate by Hilton Richmond
See all 1,071 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.

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 Center after a day of adventure.
See properties

What to do in Chesterfield

A bus tour of Richmond’s most unusual, unexpected, and humorous stories — history with a twist!

Offbeat History Tour of Richmond on a bus

￥7,314
per adult
Offbeat History Tour of Richmond on a bus
Richmond Landmark Segway Tour

Richmond Landmark Segway Tour

￥8,940
per adult
Richmond Landmark Segway Tour
Downtown Richmond Must-See Landmarks with Self-Guided Audio Tour

Downtown Richmond Must-See Landmarks with Self-Guided Audio Tour

￥1,665
per traveler
80% of travellers recommend
Downtown Richmond Must-See Landmarks with Self-Guided Audio Tour
See all activities in Chesterfield

Frequently asked questions

How much does a Chesterfield vacation package cost?
You can snap up a vacation package to this popular destination 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?
Plan your getaway for the low season and you're likely to find cheap Chesterfield vacation packages. Bear in mind that school vacation 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 vacation. 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 vacation package to Chesterfield?
From cool attractions such as Castlewood and Magnolia Grange to its epic history, a Chesterfield vacation guarantees an unforgettable adventure. With so much to do and see, 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. Pick your travel dates: What you'd like to do in Chesterfield and your preferred season will help you decide when to go.
  2. 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.
  3. Decide how long to go for: Now that you know more about Chesterfield, you can figure out the right length of your vacation. Put together a draft itinerary and allocate enough time to get through everything on your must-do list.
  4. Bundle your airfare and accommodations: Once you've nailed down your trip dates and duration, lock in the right Chesterfield vacation package for you.

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.