Chesterfield Vacations from $305

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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.
Graduate by Hilton Richmond

Graduate by Hilton Richmond

4 out of 5
Downtown Richmond
Save 100% on your flight
Price was $451, price is now $305 per person
$305
per person
Dec 9 - Dec 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
8.4/10 Very Good! (1,374 reviews)
Great staff and very clean

Reviewed on Nov 6, 2025

Whispering Pines by Hotel O Whitestone VA

Whispering Pines by Hotel O Whitestone VA

2.5 out of 5
Price was $626, price is now $478 per person
$478
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
6.2/10 (143 reviews)
Not bad for a mid century motel. Room was small but I would call it european. Bathroom dated but clean. Needed a light bulb in shower, lampshade for table lamp, and smoke detector hooked up. When we checked in we had to air it out because of the sanitation smell but other than that I would stay again.

Reviewed on Oct 13, 2025

The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was $458, price is now $355 per person
$355
per person
Dec 9 - Dec 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
8.8/10 Excellent! (1,294 reviews)
Staff 99% incredible! From desk to server, with valets amazing except one which is extremely high!! Servers went out of way after exhausting day! I wish I got everyone’s names. I wake up during night, then go outside , I felt safe with the valet staff! Bummed that we were told 2 Queen beds several times and website, yet they are only doubles.

Reviewed on Nov 4, 2025

Country Inn & Suites by Radisson, Ashland - Hanover, VA

Country Inn & Suites by Radisson, Ashland - Hanover, VA

3 out of 5
Price was $645, price is now $517 per person
$517
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
9/10 Wonderful! (1,021 reviews)
It was a very quiet stay. Could not hear other guests on the floor. Rooms were clean and comfortable. Breakfast and coffee were good.

Reviewed on Oct 29, 2025

DoubleTree by Hilton Richmond - Midlothian

DoubleTree by Hilton Richmond - Midlothian

4 out of 5
North Chesterfield
Price was $530, price is now $429 per person
$429
per person
Jan 18 - Jan 22
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Richmond (RIC)
8/10 Very Good! (1,002 reviews)
Everything in general was great. The cleanness , the food , the staff. My kid enjoyed the indoor pool with his friends. Comfortable beds. Thanks

Reviewed on Nov 2, 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

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

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

Historic Trolley Tour

Historic Trolley Tour

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

Chesterfield Hotel Deals

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
$163 nightly
The price is $190 total per night from Nov 17 to Nov 18
$190 total
Nov 17 - Nov 18
Total with taxes and fees
8.2/10 Very Good! (1,387 reviews)
Yes very much so

Reviewed on Nov 1, 2025

Graduate by Hilton Richmond
The Jefferson Hotel

The Jefferson Hotel

5 out of 5
101 West Franklin Street, Richmond, VA
Fully refundableReserve now, pay when you stay
$305 nightly
The price is $355 total per night from Nov 23 to Nov 24
$355 total
Nov 23 - Nov 24
Total with taxes and fees
9.8/10 Exceptional! (1,022 reviews)
great men at the arrival to get car to valet

Reviewed on Nov 3, 2025

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
$151 nightly
The price is $176 total per night from Nov 23 to Nov 24
$176 total
Nov 23 - Nov 24
Total with taxes and fees
9/10 Wonderful! (1,226 reviews)
The staff was pleasant and professional. We arrived several hours early before check-in and granted

Reviewed on Nov 4, 2025

Omni Richmond Hotel
See all 945 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 $305 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.