Chesterfield Vacations from $214

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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.
Patriots Inn

Patriots Inn

2.5 out of 5
Price was $304, price is now $214 per person
$214
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Richmond (RIC)
9.4/10 Exceptional! (1,007 reviews)
The room was great. Clean and plenty of space. No problems at all during our stay. Will book this inn again gor our next trip to Williamsburg.

Reviewed on Dec 1, 2025

Griffin Hotel, an official Colonial Williamsburg Hotel

Griffin Hotel, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
Save 100% on your flight
Price was $448, price is now $279 per person
$279
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Richmond (RIC)
8.8/10 Excellent! (765 reviews)
Our check-in was delayed an hour due to being at max capacity however, due to the close proximity to Merchant's Square, we walked down and enjoyed mulled wine at the Christmas Market until we were notified to check-in. The room is spacious and we will definitely be back!

Reviewed on Nov 29, 2025

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
Save 100% on your flight
Price was $441, price is now $301 per person
$301
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Richmond (RIC)
8.8/10 Excellent! (1,608 reviews)
Staff was wonderful! Cooling in room was not good and breakfast offered didn’t have scrambled eggs or a breakfast meat. Biscuits and gravy would have been good, or make your own waffle. Flavored creamer for the coffee would have been nice!

Reviewed on Dec 2, 2025

The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
Price was $391, price is now $271 per person
$271
per person
Feb 14 - Feb 17
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
9/10 Wonderful! (1,000 reviews)
We loved the location, and the check-in and check-out personnel were friendly and efficient. That being said, there was an ugly black stain on the carpet in the middle of the dining area. Also there was something that looked like a snot or blood stain on the wall near the TV in the living room. Also, we called the front desk to ask a question about the TV. We were told she didn’t know anything about the TVs and we would need to call maintenance about that. It was fairly late at night and we 3 women did not want a maintenance man coming since we were already relaxed and in for the night. Seems like the front desk should be able to answer a simple question about the TV operation.

Reviewed on Nov 30, 2025

Wedmore Place

Wedmore Place

3.5 out of 5
Price was $400, price is now $281 per person
$281
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Richmond (RIC)
9.4/10 Exceptional! (1,002 reviews)
Staff was great and very hospitable

Reviewed on Nov 21, 2025

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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

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

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

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
Historic Trolley Tour

Historic Trolley Tour

$42
per adult
100% of travellers recommend
Historic Trolley Tour
See all activities in Chesterfield

Chesterfield Hotel Deals

Omni Richmond Hotel

Omni Richmond Hotel

4 out of 5
100 S 12th St Richmond VA
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $197 total per night from Dec 7 to Dec 8
$197 total
Dec 7 - Dec 8
Total with taxes and fees
9/10 Wonderful! (1,261 reviews)
The hotel is beautiful! Very spacious room

Reviewed on Dec 2, 2025

Omni Richmond Hotel
The Jefferson Hotel

The Jefferson Hotel

5 out of 5
101 West Franklin Street Richmond VA
Fully refundableReserve now, pay when you stay
$295 nightly
The price is $343 total per night from Jan 1 to Jan 2
$343 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
9.8/10 Exceptional! (1,014 reviews)
Excellent dining, beautiful hotel, very convenient amenities

Reviewed on Nov 30, 2025

The Jefferson Hotel
Drury Plaza Hotel Richmond

Drury Plaza Hotel Richmond

3 out of 5
11049 West Broad St Glen Allen VA
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $128 total per night from Dec 11 to Dec 12
$128 total
Dec 11 - Dec 12
Total with taxes and fees
9.6/10 Exceptional! (2,845 reviews)
Friendly service

Reviewed on Dec 1, 2025

Drury Plaza Hotel Richmond
See all 960 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.

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

How much does a Chesterfield vacation package cost?
You can snap up a vacation package to this popular destination from $214 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?
If you're looking to snag a cheap Chesterfield vacation package, consider visiting in February, November and December. You'll generally find better rates on airfares and hotels during these months — perfect for a budget-friendly getaway.
How many days is enough for Chesterfield?
Usually, a handful of days is enough to tick off the main attractions during your Chesterfield vacation. But if you want to have time to unwind or go on day trips, consider extending your itinerary.
Is it worth booking a vacation package to Chesterfield?
From attractions such as Castlewood and Magnolia Grange to its terrific history, a Chesterfield vacation is sure to exceed your expectations. With so much to see and do, it's time to 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. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to Chesterfield.
  2. Budget wisely: As well as the price of your accommodations, you'll need to consider other expenses too. These include food, flights and transportation. Also, put aside a little extra for unexpected expenses that may come up during your trip to Chesterfield.
  3. Explore Chesterfield using our trip planning tool: Gain insights into the top attractions and best hotels for your trip to Chesterfield. You can also save your must-visit places, collaborate with friends and family and organize your plans in one place.
  4. Determine how many days away: Start by making a list of all the activities and sights you'd like to get to in Chesterfield. Then, estimate how long you'll need at each, along with any travel time.
  5. Bundle your airfare and accommodations: Once you've nailed down your trip dates and duration, book the right Chesterfield vacation package for you.
  6. Book any excursions or activities: Now to the fun part — organizing everything you want to do and see. Check out some of the top things to do in Chesterfield in Chesterfield and book your tickets early to save time (and maybe some dollars too!).

Does Expedia offer Book Now, Pay Later Chesterfield vacation packages?
If you're anything like us, you love traveling the world but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the overall cost of your Chesterfield break across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure great vacation packages with payment plans as soon as you see them.

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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.