Chesterfield Vacations from $498

Book a Hotel + Flight or Car together to unlock savings

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.

The Latest Chesterfield vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn & Suites Richmond West End

Holiday Inn & Suites Richmond West End

3 out of 5
Laurel
Price was $669, price is now $498 per person
$498
per person
Dec 5 - Dec 12
found 7 hours ago
Roundtrip flight included
Tampa (TPA) to Richmond (RIC)
8.8/10 Excellent! (739 reviews)

Westgate Historic Williamsburg Resort

Westgate Historic Williamsburg Resort

3.5 out of 5
Midtown
Price was $759, price is now $512 per person
$512
per person
Dec 11 - Dec 13
found 1 day ago
Roundtrip flight included
New York (NYC) to Richmond (RIC)
8.6/10 Excellent! (1,001 reviews)

The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was $887, price is now $653 per person
$653
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
8.8/10 Excellent! (1,419 reviews)

Holiday Inn Express Richmond I-64 Short Pump Area by IHG

Holiday Inn Express Richmond I-64 Short Pump Area by IHG

2.5 out of 5
Price was $688, price is now $515 per person
$515
per person
Dec 5 - Dec 12
found 7 hours ago
Roundtrip flight included
Tampa (TPA) to Richmond (RIC)
9/10 Wonderful! (1,221 reviews)
Everything was great, the staff was super friendly, from check in to questions about the area to check out! The room was amazing, super comfy beds, quiet rooms, and the shower was perfect with amazing water pressure! The breakfast wasn’t amazing but it was okay. There’s lots to do in the area as well! We will be back!

Reviewed on Nov 3, 2026

La Quinta Inn & Suites by Wyndham Richmond-Midlothian

La Quinta Inn & Suites by Wyndham Richmond-Midlothian

3 out of 5
North Chesterfield
Price was $687, price is now $544 per person
$544
per person
Dec 5 - Dec 12
found 7 hours ago
Roundtrip flight included
Tampa (TPA) to Richmond (RIC)
8.2/10 Very Good! (1,427 reviews)

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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

What to do in Chesterfield

Richmond: Guided Hike in James River Park

Richmond: Guided Hike in James River Park

$35
per adult
100% of travellers recommend
Richmond: Guided Hike in James River Park
Downtown Richmond Must-See Landmarks with Self-Guided Audio Tour

Downtown Richmond Must-See Landmarks with Self-Guided Audio Tour

$10
per traveler
80% of travellers recommend
Downtown Richmond Must-See Landmarks with Self-Guided Audio Tour
Historic Trolley Tour

Historic Trolley Tour

$45
per adult
100% of travellers recommend
Historic Trolley Tour
See all activities in Chesterfield

Find the Best Chesterfield Vacation Packages

Chesterfield Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Richmond Intl. Airport (RIC)
Population
3,800
Max Temp Winter
50ºF
Max Temp Summer
90ºF
Top Sights
Pocahontas State Park, Uptown Alley and Pocahontas State Park Museum

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Frequently asked questions

Is Chesterfield better suited for a beach vacation or a cultural trip?
A Chesterfield vacation is primarily suited for urban exploration, family-friendly attractions, and outdoor activities. As a central urban destination, it offers a mix of shopping, entertainment, and green spaces.

Travelers can enjoy outdoor pursuits at places like Pocahontas State Park, about 8 miles from central Chesterfield, or explore shopping and dining at Short Pump Town Center, about 14 miles away. Chesterfield provides a range of city-based experiences and recreational opportunities.
How can I save money on a Chesterfield vacation package?
When you bundle, you can save up to 30%*. To save money on a Chesterfield package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What are the top things to do in Chesterfield?
A Chesterfield vacation offers a variety of family-friendly attractions, shopping, and outdoor activities:

Browse and book things to do in Chesterfield on Expedia.
Do you need to rent a car in Chesterfield, or is public transport enough?
For a Chesterfield vacation package, renting a car offers the most flexibility to explore the area's attractions. While Chesterfield is a central urban destination, many popular sights are spread out.

For instance, Pocahontas State Park is about 8 miles from central Chesterfield, Short Pump Town Center is about 14 miles away, and Kings Dominion is about 13 miles from the center. Having a car allows you to easily reach these family-friendly attractions and other points of interest at your own pace. Travelers booking Chesterfield vacation packages with flights will find that a rental car provides convenient access from the airport and throughout the region.
Are there vacation package hotels in Chesterfield within walking distance of restaurants and shops?
A Chesterfield vacation package can include hotels conveniently located near shopping and dining areas.

Home2 Suites by Hilton Richmond Short Pump, rated 8.7 out of 10, is about a 5-minute walk from Short Pump Town Center, offering easy access to its shops and restaurants. For those near Chesterfield Towne Center, La Quinta Inn & Suites by Wyndham Richmond-Midlothian, rated 7.8 out of 10, and Hampton Inn Richmond-Midlothian Turnpike, rated 7.7 out of 10, are both about a 5-minute walk away. The 4-star DoubleTree by Hilton Richmond - Midlothian, rated 7.8 out of 10, is also about a 10-minute walk from Chesterfield Towne Center.

Actual walking routes may differ from straight-line distances, so it's always good to check the map for your selected hotel.
Can I change or cancel my Chesterfield vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Chesterfield vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Chesterfield vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Chesterfield vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Chesterfield?
To find last-minute vacation packages to Chesterfield, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Chesterfield vacation packages?
Free cancellation on a Chesterfield vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Chesterfield vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Chesterfield getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Chesterfield vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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