Chesterfield Vacation Packages

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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.

Top Chesterfield Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Linden Row Inn

Linden Row Inn

3 out of 5
Downtown Richmond
per person
Sep 15 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Richmond (RIC)
9.2/10 Wonderful! (1,123 reviews)
Friendly traditional inn

Reviewed on Aug. 11, 2025

Hilton Richmond Downtown

Hilton Richmond Downtown

4 out of 5
Downtown Richmond
per person
Sep 15 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Richmond (RIC)
8.4/10 Very Good! (1,013 reviews)
Check in was a little slow but otherwise all went well.

Reviewed on Aug. 11, 2025

Landing Apartments near Virginia Union University

Landing Apartments near Virginia Union University

3.5 out of 5
per person
Sep 15 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Richmond (RIC)
8.8/10 Excellent! (16 reviews)
Overall this property was a good place to stay so we could spread out and have extra room for our trip. Communication was fine and checkin instructions were very detailed. I cannot give it 5 stars however. The shower curtain and shower were dirty. There were stains on the bed linens and the comforter as well as a hole in the comforter. The property also charges $5/day for parking which was not disclosed in the original price. The exterior of the property had a dog area and people did not clean up after their dog — this was also the area we were required to park.

Reviewed on Jun. 29, 2025

The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
per person
Sep 15 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Richmond (RIC)
8.8/10 Excellent! (1,260 reviews)
The studio was a nice size and the view of the park was lovely.

Reviewed on Aug. 12, 2025

Graduate by Hilton Richmond

Graduate by Hilton Richmond

4 out of 5
Downtown Richmond
per person
Sep 15 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Richmond (RIC)
8.4/10 Very Good! (1,320 reviews)
Construction was overbearingly loud in the lobby area. They did give free drink tokens out because of this so that was nice. Other than painfully loud noises checking in and while waiting for my room to be ready, it was a very nice hotel. The rooftop bar was really nice and the bartender working on 8/10/25 around 4:00 pm was really good and very professional.

Reviewed on Aug. 12, 2025

Ready to book your vacation to Chesterfield?

 

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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
The price is CA $393 per night from Aug 24 to Aug 25
CA $393
CA $457 total
Aug 24 - Aug 25
includes taxes & fees
9.8/10 Exceptional! (1,009 reviews)
"Concierge and transportation staff were nothing short of amazing."

Reviewed on Aug. 12, 2025

The Jefferson Hotel
Studio 6 Richmond, VA - Airport

Studio 6 Richmond, VA - Airport

2 out of 5
580 Trampton Road, Sandston, VA
Fully refundableReserve now, pay when you stay
The price is CA $105 per night from Sep 11 to Sep 12
CA $105
CA $122 total
Sep 11 - Sep 12
includes taxes & fees
8.8/10 Excellent! (210 reviews)
"1"

Reviewed on Aug. 10, 2025

Studio 6 Richmond, VA - Airport
Omni Richmond Hotel

Omni Richmond Hotel

4 out of 5
100 S 12th St, Richmond, VA
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from Aug 24 to Aug 25
CA $208
CA $242 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,163 reviews)
"Nice"

Reviewed on Aug. 12, 2025

Omni Richmond Hotel
See all 957 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.
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Discover the most popular places to visit in Chesterfield

Pocahontas State Park

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

What to do in Chesterfield

Historic Trolley Tour

Historic Trolley Tour

CA $58
per adult
100% of travellers recommend
Historic Trolley Tour
Richmond: Guided Hike in James River Park

Richmond: Guided Hike in James River Park

CA $48
per adult
Richmond: Guided Hike in James River Park
Come see Richmond like you never have heard tales of death and bring the city's history back to life.

RVA Ghosts Shockoe Bottom Sinister Scares by US Ghost Adventures

CA $36
per adult
RVA Ghosts Shockoe Bottom Sinister Scares by US Ghost Adventures
See all activities in Chesterfield

Frequently asked questions

How much does a Chesterfield vacation package cost?
You can pick up a vacation package to this destination from CA $1,236 on Expedia. However, how much your vacation to Chesterfield costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Chesterfield?
Plan your getaway for the off-season and you're likely to find cheap Chesterfield vacation packages. Remember that public holidays and major local events can have an impact on prices, so do a little research before booking.
How many days is enough for Chesterfield?
With a well-organized schedule, you can easily visit the main Chesterfield sights in a handful of days. But if you prefer to discover lesser-known spots or go on day tours, consider booking your Chesterfield vacation for longer.
Is it worth booking a vacation package to Chesterfield?
Boasting a host of highlights starting with its top-notch history, Chesterfield is a good vacation destination. Whether you'd like to check out attractions like Castlewood and Magnolia Grange or venture off the beaten track, you'll find plenty to see and do on your Chesterfield vacation.
How to find the best Chesterfield package deals?
Use Expedia's filter tool to help you find some of the best Chesterfield package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for Chesterfield package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Chesterfield vacation as a package?
You can enjoy significant savings on your Chesterfield getaway by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to view some great flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Chesterfield?
Enjoy incredible bargains by reserving your flights ahead of time with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Chesterfield escape.
How to plan a trip to Chesterfield?

  1. Choose when to get away: Check your calendar and get your bags packed. Your preferred time of year and the type of activities available will also help you decide when to vacation in Chesterfield.
  2. Set your budget: Consider expenses like flights, food and transportation when working out how much to save for your trip to Chesterfield. Then, select a property that suits your budget, whether that's a wallet-friendly option or a lavish retreat.
  3. Decide how long to go away for: Now that you're up to speed on Chesterfield, you can work out the perfect length of your vacation. Create a rough itinerary and allocate enough time to cover everything you want to do.
  4. Combine your airfare and accommodations: After you've nailed down your trip dates and duration, lock in the ideal Chesterfield vacation package for you.

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