Chesterfield County Vacation Packages
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Your Chesterfield County Vacation
Make planning your next big getaway simple with a Chesterfield County vacation package. Whether it's nature, history or something else entirely that lures you to this destination, our package deals will help you discover it all. During your trip to Chesterfield County, you'll want to tick off some of its most popular cities. What shouldn't you miss? Brandermill. From the instant you book your Chesterfield County vacation to when you get back home, Expedia will be with you each step of the way.
Top Chesterfield County Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
Colonial Williamsburg
CA $1,076
per person
Dec 17 - Dec 22
found 6 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Richmond (RIC)
8.8/10 Excellent! (2,000 reviews)
Next door to the Colonial Williamsburg Visitor Center, which is a great benefit. The hotel also has a free daily breakfast, though there is little variation in what is served. For example, we had seven breakfasts there, and no bacon was ever served.
The room was quiet, and the hotel provides daily room service—which I have not seen since before Covid. The maid staff is friendly and willing to work with the guests.
Reviewed on Oct 13, 2026
Kingsmill Resort
Kingsmill
CA $1,469
per person
Dec 20 - Dec 26
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.6/10 Excellent! (1,006 reviews)
Room was big (one bedroom condo) and clean. However, it needs more proper maintenance. Some lights (lamp, overhead) were burned out and have not been replaced. The toilet is not properly attached to the floor (it moves when you sit).
Reviewed on Oct 14, 2026
Chesterfield County Hotel Deals
La Quinta Inn & Suites by Wyndham Richmond-Midlothian
1301 Huguenot Road Midlothian VA
Fully refundableReserve now, pay when you stay
CA $139
CA $165 total
Oct 18 - Oct 19
includes taxes & fees
8.2/10 Very good! (1,413 reviews)
"The staff was polite, friendly and welcoming. As soon as I got off of the elevator, the smell hit me and I was like this smells so good. I'm definitely returning for future stays"
Reviewed on Oct 13, 2026
Four Points by Sheraton Richmond
9901 Midlothian Tpke Richmond VA
CA $141
CA $164 total
Nov 4 - Nov 5
includes taxes & fees
Hyatt Place Richmond/Arboretum
201 Arboretum Place Richmond VA
CA $156
CA $182 total
Oct 25 - Oct 26
includes taxes & fees
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 County vacation package cost?
Live it up in Chesterfield County from just CA $1,076. Choose from a wonderful selection of flights, hotels and rental cars to suit your budget. You can score even more discounts when you add a few sightseeing tours to your vacation package.
How do I get a cheap travel package to Chesterfield County?
Crafting your own Chesterfield County vacation package with Expedia is a smart way to save. We have more than 550 partner airlines and 1,000,000 properties globally. With such a fantastic range to pick from, you'll have no worries pulling together your dream escape.
What are the top hotels in Chesterfield County?
For properties in Midlothian with cozy beds and friendly service, you can't go past La Quinta Inn & Suites by Wyndham Richmond-Midlothian and Hyatt Place Richmond/Arboretum. If you plan to visit Chesterfield as well, you can look forward to a wonderful night's sleep at Country Inn & Suites by Radisson, Richmond I-95 South, VA or DoubleTree by Hilton Richmond - Midlothian.
How far in advance should I book my Chesterfield County vacation?
Reserving your spot early with Expedia means one less thing to worry about. Most air carriers advertise tickets up to 12 months prior to departure dates. Typically, this is the cheapest time to book. If circumstances have left you booking late, last-minute deals to Chesterfield County will sometimes occur just weeks before departure.
What does an Expedia Chesterfield County travel package include?
Rental cars, hotels and flights, or any combination of them — the choice is all yours! Whether you're headed to Chesterfield County with the whole family or traveling by yourself, there's a package to suit your style and budget. Once you've made your booking, why not add on some tours or activities?
What should I know before booking a Chesterfield County travel package?
Whether it's relaxation or adventure you're after, a Chesterfield County vacation package lets you plan your escape your way. Plus, you'll get access to great discounts when you combine your accommodations with your flights and rental car. The more you bundle, the bigger the savings!
Can I choose my airline with a Chesterfield County Expedia vacation package?
With a vacation package, you're always in charge. Whether you'd prefer to fly to Chesterfield County in economy or business class, simply pick from the available airline options. Expedia has access to over 550 airline partners worldwide.
If I'm not able to travel, can I cancel my Chesterfield County vacation package?
Whether it's your flight or hotel, you can cancel or alter it. Locked in your Chesterfield County vacation package in the last 24 hours? You may be able to make changes or cancellations at no cost. For bookings made more than 24 hours ago, you may incur a fee from your hotel, airline or car rental company. For further information, look up our Customer Service Portal. We're here to help you every step of the way.
Stay near popular Chesterfield County attractions
Chesterfield Towne Center
8.4/10 (110 reviews)
You can browse for the perfect souvenirs at Chesterfield Towne Center during your trip to Richmond. Amble around this family-friendly area's picturesque gardens or attend a sporting event.
Pocahontas State Park
8.4/10 (31 reviews)
You can take time to visit Pocahontas State Park during your travels to Chesterfield. Attend a sporting event in this family-friendly area.
Metro Richmond Zoo
8.0/10 (6 reviews)
See the exotic and native animals who live at Metro Richmond Zoo during your travels in Moseley. Attend a sporting event in this family-friendly area.
River City Sportsplex
9.4/10 (31 reviews)
Catch an event at River City Sportsplex during your trip to Midlothian. Visit the shops in this family-friendly area, or simply enjoy its restaurants.
Rogers Stadium
7.4/10 (27 reviews)
Catch an event at Rogers Stadium during your trip to Petersburg. While you're in the area, stroll along the riverfront.
Rockwood Park
You can take time to visit Rockwood Park during your travels to Richmond. Attend a sporting event in this family-friendly area.
Castlewood
8.0/10 (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.
Southside Speedway
7.6/10 (12 reviews)
Catch an event at Southside Speedway during your trip to Midlothian. Attend a sporting event in this family-friendly area.
What to do in Chesterfield County
Richmond: Guided Hike in James River Park
CA $49
per adult
100% of travellers recommend
Downtown Richmond Must-See Landmarks with Self-Guided Audio Tour
CA $14
per traveller
80% of travellers recommend
Richmond Ghost Tour: Sinister Secrets of Shockoe Bottom
CA $36
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
