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
Price was CA $1,705, price is now CA $1,253 per person
CA $1,253
per person
Oct 9 - Oct 13
found 5 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Richmond (RIC)
9.2/10 Wonderful! (1,147 reviews)
The garden was quite escape to the city. I didnt like the parking situation. You have to park in parking garage and park in monthly to stay overnight or wake up and midnight and pay for the next day. Hotel front desk was sassy about questions we had about the parking. She was defensive. Parking is not through the hotel. Which we knew. We just needed advice. Front desk was lovely otherwise.

Reviewed on Aug. 21, 2025

Hilton Richmond Downtown

Hilton Richmond Downtown

4 out of 5
Downtown Richmond
Price was CA $1,784, price is now CA $1,356 per person
CA $1,356
per person
Oct 9 - Oct 13
found 7 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Richmond (RIC)
8.4/10 Very Good! (1,003 reviews)
It’s a very pleasant property and is located in a great area, staff were very helpful and friendly. This is my second visit. I will probably come again.

Reviewed on Aug. 22, 2025

The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was CA $1,697, price is now CA $1,290 per person
CA $1,290
per person
Oct 9 - Oct 13
found 5 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Richmond (RIC)
8.8/10 Excellent! (1,267 reviews)
Water didn’t get quite hot enough but other than a quick shower it was great - room 605

Reviewed on Aug. 22, 2025

Club Wyndham Kingsgate

Club Wyndham Kingsgate

3 out of 5
Price was CA $1,640, price is now CA $1,263 per person
CA $1,263
per person
Oct 11 - Oct 18
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,006 reviews)
It was family friendly for sure. The main building has an arcade and consoles available for play. There is an indoor pool and 2 outdoor pools. They manage the property well. I had an issue where someone backed into my car and they were able to help me out and were very nice in how they handled the situation. If you can, during your reservation get a building/room near the front of the property so you can walk to the pools. The 30s, you will have to drive. Thank you Caitlyn L. for your careful handling and service.

Reviewed on Aug. 19, 2025

The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
Price was CA $1,890, price is now CA $1,456 per person
CA $1,456
per person
Oct 11 - Oct 18
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9/10 Wonderful! (1,011 reviews)
Large 2 bedroom 2 bath exactly as pictured. Close to restaurants, Busch Gardens. Water County and Colonial Williamsburg.

Reviewed on Aug. 24, 2025

Ready to book your vacation to Chesterfield?

 

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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 $220 per night from Sep 2 to Sep 3
CA $220
CA $256 total
Sep 2 - Sep 3
includes taxes & fees
8.8/10 Excellent! (1,162 reviews)
"All was great"

Reviewed on Aug. 19, 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
The price is CA $394 per night from Sep 1 to Sep 2
CA $394
CA $458 total
Sep 1 - Sep 2
includes taxes & fees
9.8/10 Exceptional! (1,003 reviews)
A Must Stay!
"Make your reservation today! The Jefferson exceeds every expectation and beyond!! Classically and historically beautiful, impeccably maintained, superior staff. I can't wait to return!"

Reviewed on Aug. 18, 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
The price is CA $156 per night from Aug 31 to Sep 1
CA $156
CA $181 total
Aug 31 - Sep 1
includes taxes & fees
9.6/10 Exceptional! (2,720 reviews)
"We've been here a dozen or more times. It really is a great place with great employees!"

Reviewed on Aug. 21, 2025

Drury Plaza Hotel Richmond
See all 935 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 $1,253 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.