Chesterfield Holidays

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Your Chesterfield Holiday

Say farewell to planning hassles and hello to a Chesterfield holiday package. With everything organised before you go, you can focus on discovering every inch of this city, starting with Downtown Richmond, which is good for cafes, nightlife and festivals. If your trip to Chesterfield includes some sightseeing, take in well-known attractions like Pocahontas State Park, Castlewood and Pocahontas State Park Museum. Stop dreaming and start doing. Explore the multitude of options on Expedia today and put your Chesterfield holiday plans into gear!

Chesterfield Holiday

Chesterfield Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Richmond Intl. Airport (RIC)
Population
3,800
Max Temp Winter
10ºC
Max Temp Summer
32ºC
Top Sights
Pocahontas State Park, Uptown Alley and Pocahontas State Park Museum

Our pick of the best Chesterfield Hotel Deals

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 AU$285 per night from 2 Sept to 3 Sept
AU$285
2 Sept - 3 Sept
includes taxes & fees
8.8/10 Excellent! (1,161 reviews)
"All was great"

Reviewed on 19 Aug. 2025

Omni Richmond Hotel
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 AU$511 per night from 2 Sept to 3 Sept
AU$511
2 Sept - 3 Sept
includes taxes & fees
9.8/10 Exceptional! (1,001 reviews)
A Must Stay!
"Make your reservation today! The Jefferson exceeds every expectation and beyond!! Classically and historically beautiful, impeccably maintained, superior staff. I can't wait to return!"

Reviewed on 18 Aug. 2025

The Jefferson 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
The price is AU$202 per night from 31 Aug to 1 Sept
AU$202
31 Aug - 1 Sept
includes taxes & fees
9.6/10 Exceptional! (2,720 reviews)
"We've been here a dozen or more times. It really is a great place with great employees!"

Reviewed on 21 Aug. 2025

Drury Plaza Hotel Richmond
See all 935 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

What to do in Chesterfield

Historic Trolley Tour

Historic Trolley Tour

AU$64
per adult
100% of travellers recommend
Historic Trolley Tour
Richmond: Guided Hike in James River Park

Richmond: Guided Hike in James River Park

AU$54
per adult
Richmond: Guided Hike in James River Park
Come see Richmond like you never have heard tales of death and bring the city's history back to life.

RVA Ghosts Shockoe Bottom Sinister Scares by US Ghost Adventures

AU$40
per adult
RVA Ghosts Shockoe Bottom Sinister Scares by US Ghost Adventures
See all activities in Chesterfield

Frequently asked questions

How much does a Chesterfield holiday package cost?
You can snap up a holiday package to this popular destination on Expedia. However, how much your holiday 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 holiday packages. Bear in mind that school holiday 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 holiday. 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 holiday package to Chesterfield?
From cool attractions such as Castlewood and Magnolia Grange to its epic history, a Chesterfield holiday guarantees an unforgettable adventure. With so much to do and see, find out for yourself why Chesterfield is such a good holiday 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 holiday as a package?
An Expedia holiday 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 holiday 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 holiday.
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 holiday. Put together a draft itinerary and allocate enough time to get through everything on your must-do list.
  4. Bundle your airfare and accommodation: Once you've nailed down your trip dates and duration, lock in the right Chesterfield holiday package for you.

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