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.
Wingate by Wyndham Richmond Short Pump

Wingate by Wyndham Richmond Short Pump

2.5 out of 5
Short Pump
per person
Jun. 12 - Jun. 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.6/10 Excellent! (1,813 reviews)
Breakfast should have been much better , and a

Reviewed on Apr. 28, 2025

Warner Hall

Warner Hall

3 out of 5
Save 100% on your flight
per person
Jun. 8 - Jun. 15
found 19 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Richmond (RIC)
10/10 Exceptional! (1 review)
Beautiful, tranquil property with lovely rooms. Staff was friendly and helpful, and the breakfasts were delicious.

Reviewed on Apr. 23, 2025

Fort Magruder Historic Williamsburg, Trademark by Wyndham

Fort Magruder Historic Williamsburg, Trademark by Wyndham

3.5 out of 5
per person
Jul. 21 - Jul. 28
found 22 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Richmond (RIC)
7.2/10 Good! (1,379 reviews)
The odd thing was the lobby sermed nice, clean & updated. However, our room was old & dark. Simple things like bathroom lighting would even make a difference.

Reviewed on Apr. 29, 2025

Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
per person
Jul. 21 - Jul. 28
found 22 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Richmond (RIC)
8.8/10 Excellent! (1,003 reviews)
I was expecting more from the room accommodations, because of the price. The restaurant was very nice with excellent service. Pricey as to be expected. However, the room was really dated and mediocre. Almost had a dingy feel. It had two landline phones, one even in the bathroom (lol), and neither worked. I drove around to 3 different locations to find ice, bc 2 out of the 3 machines were broken. The only reason I’d stay here again is if I got a really good deal. The rooms really need some updating.

Reviewed on Apr. 25, 2025

Barsala At Sphere Apartments

Barsala At Sphere Apartments

3.5 out of 5
per person
Jun. 12 - Jun. 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9.2/10 Wonderful! (9 reviews)
This was a clean, well-equipped and comfortable apartment. The location is good but does require a car to explore the city and pick up groceries. Parking was easy and free. The balcony was a nice place to sit as the temperature got warmer. Air conditioning was very effective. Would stay again.

Reviewed on Apr. 24, 2025

Ready to book your vacation to Chesterfield?

 

Choose your dates

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
The price is CA $231 per night from May 22 to May 23
CA $231
CA $269 total
includes taxes & fees
May 22 - May 23
8.8/10 Excellent! (1,126 reviews)
"Nice place"

Reviewed on Apr. 28, 2025

Omni Richmond Hotel
Regency Inn Richmond
Regency Inn Richmond
2 out of 5
1500 Eastridge Road, Richmond, VA
Fully refundableReserve now, pay when you stay
The price is CA $81 per night from May 3 to May 4
CA $81
CA $95 total
includes taxes & fees
May 3 - May 4
6.6/10 (1,002 reviews)
"Very quite . Older hotel. Lots of stores near by. Would stay there again"

Reviewed on Apr. 30, 2025

Regency Inn Richmond
The Commonwealth
The Commonwealth
4 out of 5
901 Bank St, Richmond, VA
The price is CA $193 per night from May 26 to May 27
CA $193
CA $225 total
includes taxes & fees
May 26 - May 27
8.8/10 Excellent! (1,228 reviews)
"Great rooms, small elevators"

Reviewed on Apr. 29, 2025

The Commonwealth
See all 951 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Chesterfield vacation package cost?
You can pick up a vacation package to this destination from CA $736 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.

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
Historic Trolley Tour
“Our guide was awesome, kind and very knowledgeable about the area and each restaurant. I highly recommend this company and we will be taking the other tours they offer.” - River City Food Tours guest

Arts District Food Tour in Richmond with Discover Richmond

CA $130
per adult
Arts District Food Tour in Richmond with Discover Richmond
Richmond: Guided Hike in James River Park

Richmond: Guided Hike in James River Park

CA $40
per adult
Richmond: Guided Hike in James River Park
See all activities in Chesterfield
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.