Chesterfield Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Chesterfield

Regency Inn Richmond
Regency Inn Richmond
2 out of 5
1500 Eastridge Road, Richmond, VA
Fully refundableReserve now, pay when you stay
The price is 1.763.842 ₫ per night from 28 Jun to 29 Jun
1.763.842 ₫
2.050.995 ₫ total
28 Jun - 29 Jun
includes taxes & fees
7/10 Good! (1,002 reviews)
"I love staying here and it’s quiet and peaceful"

Reviewed on 16 Jun 2025

Regency Inn Richmond
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 3.951.007 ₫ per night from 2 Jul to 3 Jul
3.951.007 ₫
4.594.231 ₫ total
2 Jul - 3 Jul
includes taxes & fees
8.8/10 Excellent! (1,124 reviews)
"cool ."

Reviewed on 17 Jun 2025

Omni Richmond Hotel
Red Roof Inn Richmond South
Red Roof Inn Richmond South
2 out of 5
4350 Commerce Rd, Richmond, VA
Fully refundableReserve now, pay when you stay
The price is 1.645.992 ₫ per night from 29 Jun to 30 Jun
1.645.992 ₫
1.914.096 ₫ total
29 Jun - 30 Jun
includes taxes & fees
6.4/10 (1,000 reviews)
"Great hotel, good service, my only issue is they need to change the air conditioner filters in certain rooms."

Reviewed on 19 Jun 2025

Red Roof Inn Richmond South
See all 955 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.

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.

Popular places to visit

Pocahontas State Park

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 when you stop by Castlewood. Stroll along the riverfront or attend a sporting event in the area.

Castlewood

Pocahontas State Park Museum

You can spend an afternoon exploring the galleries in Pocahontas State Park Museum during your travels in Chesterfield. Take in the live music in this family-friendly area.

Pocahontas State Park Museum