Two cannons in a grassy field with trees and a fence in the background.

Chesterfield Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Your Chesterfield Vacation

Lock in a Chesterfield vacation package that includes everything you need and no unnecessary extras. Great for nightlife, cafes and festivals, think about basing yourself in the neighborhood of Downtown Richmond. A trip to Chesterfield is a wonderful opportunity to see the sights. Be sure to stop by big-name attractions such as Pocahontas State Park, Castlewood and Magnolia Grange. Expedia has what you need to escape your daily routine. Tailor your vacation to Chesterfield to suit your style of travel, whatever that may look like.

Top Chesterfield vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Dec 18 - Dec 22

    Omni Richmond Hotel + Flight

    Downtown Richmond
    4 nights
    4.0 star property
    9.2/10 - Wonderful (1,593 reviews)
    "Great experience"
    Reviewed November 9, 2026
    Roundtrip • Buffalo (BUF) - Richmond (RIC)
    BUF - RIC • 1 stop RIC - BUF • 1 stop
    CA $1,179
    CA $1,060
    per traveller
    found 1 day ago
    Omni Richmond Hotel
  • Dec 18 - Dec 22

    The Commonwealth + Flight

    Downtown Richmond
    4 nights
    4.0 star property
    8.8/10 - Excellent (1,416 reviews)
    "*"
    Reviewed November 9, 2026
    Roundtrip • Buffalo (BUF) - Richmond (RIC)
    BUF - RIC • 1 stop RIC - BUF • 1 stop
    CA $1,453
    CA $1,108
    per traveller
    found 1 day ago
    The Commonwealth
  • Dec 21 - Dec 26

    Kings Creek Plantation by TripForth + Flight

    Williamsburg
    5 nights
    3.5 star property
    8.6/10 - Excellent (44 reviews)
    "Beautiful property!!"
    Reviewed August 2, 2026
    Roundtrip • Halifax (YHZ) - Richmond (RIC)
    YHZ - RIC • 1 stop RIC - YHZ • 2 stops
    CA $2,039
    CA $1,825
    per traveller
    found 10 hours ago
    Kings Creek Plantation by TripForth
  • Dec 23 - Dec 27

    Kingsmill Resort + Flight

    Kingsmill
    4 nights
    4.0 star property
    8.6/10 - Excellent (1,002 reviews)
    "Everything about the experience was fantastic!"
    Reviewed November 9, 2026
    Roundtrip • Montreal (YMQ) - Richmond (RIC)
    YUL - RIC • 1 stop RIC - YUL • 1 stop
    CA $1,836
    CA $1,656
    per traveller
    found 1 day ago
    Kingsmill Resort
  • Dec 21 - Dec 26

    Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort + Flight

    Williamsburg
    5 nights
    3.5 star property
    9.4/10 - Exceptional (424 reviews)
    Roundtrip • Halifax (YHZ) - Richmond (RIC)
    YHZ - RIC • 1 stop RIC - YHZ • 2 stops
    CA $1,268
    CA $1,159
    per traveller
    found 10 hours ago
    Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

Where to stay in Chesterfield

Find the best Chesterfield areas and neighborhoods for the activities you enjoy most.

Hampton Park

Though Hampton Park might not have many top sights, you can venture to the surrounding area to see attractions like Metro Richmond Zoo and Uptown Alley.

Discover the most popular places to visit in Chesterfield

What to do in Chesterfield

Chesterfield Hotel Deals

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 pick up a vacation package to this destination from CA $1,060 on Expedia. However, how much your vacation to Chesterfield costs will depend on factors like your hotel choice, length of stay and season.

What are the cheapest months to go to Chesterfield?

Plan your getaway for the off-season and you're likely to find cheap Chesterfield vacation packages. Remember that public holidays and major local events can have an impact on prices, so do a little research before booking.

How many days is enough for Chesterfield?

With a well-organized schedule, you can easily visit the main Chesterfield sights in a handful of days. But if you prefer to discover lesser-known spots or go on day tours, consider booking your Chesterfield vacation for longer.

Is it worth booking a vacation package to Chesterfield?

Boasting a host of highlights starting with its top-notch history, Chesterfield is a good vacation destination. Whether you'd like to check out attractions like Castlewood and Magnolia Grange or venture off the beaten track, you'll find plenty to see and do on your Chesterfield vacation.

How to find the best Chesterfield package deals?

Use Expedia's filter tool to help you find some of the best Chesterfield package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for Chesterfield package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.

Is it cheaper to book a Chesterfield vacation as a package?

You can enjoy significant savings on your Chesterfield getaway by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to view some great flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.

When to book a vacation package to Chesterfield?

Enjoy incredible bargains by reserving your flights ahead of time with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Chesterfield escape.

How to plan a trip to Chesterfield?

  1. Choose when to get away: Check your calendar and get your bags packed. Your preferred time of year and the type of activities available will also help you decide when to vacation in Chesterfield.
  2. Set your budget: Consider expenses like flights, food and transportation when working out how much to save for your trip to Chesterfield. Then, select a property that suits your budget, whether that's a wallet-friendly option or a lavish retreat.
  3. Decide how long to go away for: Now that you're up to speed on Chesterfield, you can work out the perfect length of your vacation. Create a rough itinerary and allocate enough time to cover everything you want to do.
  4. Combine your airfare and accommodations: After you've nailed down your trip dates and duration, lock in the ideal 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.