Chesterfield Vacations

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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 ₩419,348 per night from Aug 23 to Aug 24
₩419,348
₩487,617 total
Aug 23 - Aug 24
includes taxes & fees
9.8/10 Exceptional! (1,002 reviews)
"The Jefferson Hotel is one of a vanishing breed of grand historic hotels that still provide the kind of hotel experience that was already becoming rare 50 years ago. The staff are friendly and attentive, the rooms are extremely well appointed, the public spaces of the hotel are spectacular, and the ..."

Reviewed on Aug 5, 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 ₩216,224 per night from Aug 9 to Aug 10
₩216,224
₩251,425 total
Aug 9 - Aug 10
includes taxes & fees
9/10 Wonderful! (1,516 reviews)
"The Omni hotel was amazing!!! Im very picky about where I stay on vacation and Omni exceeded my expectation. The staff was super friendly and knowledgeable.Place was clean. I would go back there everytime I go to VA"

Reviewed on Aug 6, 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 ₩196,994 per night from Aug 12 to Aug 13
₩196,994
₩229,066 total
Aug 12 - Aug 13
includes taxes & fees
8.4/10 Very Good! (1,414 reviews)
"Hotel was very clean, comfortable, and had a great location! Valet parking got a bit backed up at times, especially around check-in time on a Friday. Once checked in, there was a website link you could use to order the car in advance. When I did that it was always ready when I requested it."

Reviewed on Aug 6, 2026

Graduate by Hilton Richmond
See all 1,070 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

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.

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