Chesterfield Vacations from $302

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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.
The Grey Swan Inn

The Grey Swan Inn

2 out of 5
Price was $365, price is now $302 per person
$302
per person
Sep 25 - Sep 27
found 23 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
9.4/10 Exceptional! (27 reviews)
Very clean, and smelled wonderful. Only reason for Four instead of Five is no place to sit in the room, except the bed. There’s room for one. Overall I’d recommend it.

Reviewed on May 24, 2026

Wedmore Place

Wedmore Place

3.5 out of 5
Price was $1,156, price is now $838 per person
$838
per person
Aug 28 - Sep 3
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
9.4/10 Exceptional! (1,000 reviews)
Cool place.

Reviewed on Jul 13, 2026

The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
Price was $647, price is now $504 per person
$504
per person
Aug 14 - Aug 17
found 5 hours ago
Roundtrip flight included
New York (JFK) to Richmond (RIC)
9/10 Wonderful! (1,008 reviews)
This was an amazing place and was priced very reasonably.

Reviewed on Jul 13, 2026

Courtyard by Marriott Richmond Airport

Courtyard by Marriott Richmond Airport

3 out of 5
Price was $681, price is now $548 per person
$548
per person
Sep 22 - Sep 25
found 10 hours ago
Roundtrip flight included
New York (NYC) to Richmond (RIC)
8.4/10 Very Good! (1,001 reviews)
Property is under renovation.

Reviewed on Jul 12, 2026

MV GiaMaria

MV GiaMaria

3.5 out of 5
Price was $808, price is now $654 per person
$654
per person
Sep 22 - Sep 25
found 10 hours ago
Roundtrip flight included
New York (NYC) to Richmond (RIC)
9.2/10 Wonderful! (16 reviews)
We liked the coziness of the boat, the views of the river, the surrounding areas were beautiful. The only negative thing we could say was that due to the ran/wind the boat creaked and it made it hard to sleep for one of our nights.

Reviewed on Oct 16, 2023

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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

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
$295 nightly
The price is $343 total per night from Jul 19 to Jul 20
$343 total
Jul 19 - Jul 20
Total with taxes and fees
9.8/10 Exceptional! (1,012 reviews)
"Excellent place to stay. My go to when in town."

Reviewed on Jul 15, 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
$179 nightly
The price is $208 total per night from Jul 19 to Jul 20
$208 total
Jul 19 - Jul 20
Total with taxes and fees
9/10 Wonderful! (1,483 reviews)
"Very nicd hotel in downtown Richmond. Close to many good restaurants, and some fast food chains. The property si very clean and the staff is very professinal and courteous. This was just a three-night trip, but I'd come back and stay again at the OMNI."

Reviewed on Jul 14, 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
$139 nightly
The price is $161 total per night from Aug 2 to Aug 3
$161 total
Aug 2 - Aug 3
Total with taxes and fees
8.4/10 Very Good! (1,390 reviews)
"Pretty nice"

Reviewed on Jul 15, 2026

Graduate by Hilton Richmond
See all 1,071 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 $302 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.