Chesterfield Vacations

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Find the Best Chesterfield Vacation Packages

Chesterfield Hotel Deals

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 AED 248 per night from Jun 20 to Jun 21
AED 248
AED 288 total
20 Jun - 21 Jun
includes taxes & fees
6.8/10 (1,017 reviews)
Thank you
"Hotel was good for me and my family through the whole stay front desk attendants Megan and Victoria were always helpful along with the rest of the staff. This will always be a top choice on hotels for us in the future thank you"

Reviewed on 9 June 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 AED 555 per night from Jun 29 to Jun 30
AED 555
AED 646 total
29 Jun - 30 Jun
includes taxes & fees
8.8/10 Excellent! (1,126 reviews)
"A great hotel experience. We’ve already scheduled a return visit. Room was very clean and comfortable. Staff was amazingly helpful and responsive. It was located right across the street from our destination."

Reviewed on 4 June 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 AED 231 per night from Jun 15 to Jun 16
AED 231
AED 269 total
15 Jun - 16 Jun
includes taxes & fees
6.4/10 (1,003 reviews)
"Everything was amazing"

Reviewed on 7 June 2025

Red Roof Inn Richmond South
See all 947 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 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 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.

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

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

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

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