Chesterfield County Vacation Packages

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Your Chesterfield County Vacation

Make planning your next big getaway simple with a Chesterfield County vacation package. Whether it's nature, history or something else entirely that lures you to this destination, our package deals will help you discover it all. During your trip to Chesterfield County, you'll want to tick off some of its most popular cities. What shouldn't you miss? Brandermill. From the instant you book your Chesterfield County vacation to when you get back home, Expedia will be with you each step of the way.

Top Chesterfield County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Hotel & Suites Williamsburg-Historic Gateway by IHG

Holiday Inn Hotel & Suites Williamsburg-Historic Gateway by IHG

3 out of 5
Price was CA $1,325, price is now CA $1,052 per person
CA $1,052
per person
Jul 25 - Jul 31
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
9/10 Wonderful! (1,005 reviews)
Hot tub and vending machines have been removed. Dinner menu is extremely minimal. Staff was friendly and room was clean.

Reviewed on May 1, 2026

Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
Price was CA $1,935, price is now CA $1,447 per person
CA $1,447
per person
Jul 25 - Jul 31
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (1,002 reviews)
The amenities were nice, the beds were firm but comfortable. The bathroom was a little dirty. We called to request ice that never came. Property was beautifully maintained and staff were very nice.

Reviewed on May 17, 2026

Kings Creek Plantation by TripForth

Kings Creek Plantation by TripForth

3.5 out of 5
Price was CA $2,108, price is now CA $1,788 per person
CA $1,788
per person
Jul 25 - Jul 31
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.6/10 Excellent! (42 reviews)
This was probably the best property that I've stayed at, maybe ever. I had a family of 8 and the two apartments that we shared were perfect. I will be staying here again

Reviewed on Jul 13, 2025

King’s Creek Resort by Spinnaker

King’s Creek Resort by Spinnaker

4.5 out of 5
Price was CA $1,626, price is now CA $1,384 per person
CA $1,384
per person
Jul 25 - Jul 31
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (160 reviews)
Everything was great accept going up and down the stairs with our luggage to get in the lower towns section. My husband and I both have lower back problems and my mother has congested heart disease. Everything else was great.

Reviewed on May 12, 2026

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
Price was CA $1,362, price is now CA $1,176 per person
CA $1,176
per person
Jul 25 - Jul 31
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (1,713 reviews)
This hotel is extremely dated. They have a lot to offer to do on campus, but it’s not kept up with. The mini golf course was great, but you could tell that no one goes and brushes off the green areas, which makes it harder for kids to golf. The room was nice, but the beds were crap. Just needs a full makeover. The best and most positive thing is the location and the staff.

Reviewed on May 17, 2026

Chesterfield County Hotel Deals

La Quinta Inn & Suites by Wyndham Richmond-Midlothian

La Quinta Inn & Suites by Wyndham Richmond-Midlothian

3 out of 5
1301 Huguenot Road Midlothian VA
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from May 31 to Jun 1
CA $148
CA $176 total
May 31 - Jun 1
includes taxes & fees
8.2/10 Very Good! (1,469 reviews)
Very clean room. Friendly staff. Breakfast was monitored for any replenishments needed. Ample parking. Overall, a pleasant experience.

Reviewed on May 17, 2026

La Quinta Inn & Suites by Wyndham Richmond-Midlothian
Hyatt Place Richmond/Arboretum

Hyatt Place Richmond/Arboretum

3 out of 5
201 Arboretum Place Richmond VA
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from May 31 to Jun 1
CA $151
CA $175 total
May 31 - Jun 1
includes taxes & fees
8/10 Very Good! (1,003 reviews)
The property was beautiful and welcoming. Spacious rooms. The staff was very efficient and helpful. I would definitely recommend to others whether you're traveling for business or pleasure.

Reviewed on May 14, 2026

Hyatt Place Richmond/Arboretum
Four Points by Sheraton Richmond

Four Points by Sheraton Richmond

3.5 out of 5
9901 Midlothian Tpke Richmond VA
Fully refundableReserve now, pay when you stay
The price is CA $161 per night from May 31 to Jun 1
CA $161
CA $187 total
May 31 - Jun 1
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
It was a good spot to stop and spend the night during my travels

Reviewed on May 17, 2026

Four Points by Sheraton Richmond
See all 1,148 properties in Chesterfield County
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
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Beach Vacations
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Frequently asked questions

How much does a Chesterfield County vacation package cost?
Live it up in Chesterfield County from just CA $1,052. Choose from a wonderful selection of flights, hotels and rental cars to suit your budget. You can score even more discounts when you add a few sightseeing tours to your vacation package.
How do I get a cheap travel package to Chesterfield County?
Crafting your own Chesterfield County vacation package with Expedia is a smart way to save. We have more than 550 partner airlines and 1,000,000 properties globally. With such a fantastic range to pick from, you'll have no worries pulling together your dream escape.
What are the top hotels in Chesterfield County?
For properties in Midlothian with cozy beds and friendly service, you can't go past La Quinta Inn & Suites by Wyndham Richmond-Midlothian and Hyatt Place Richmond/Arboretum. If you plan to visit Chesterfield as well, you can look forward to a wonderful night's sleep at Country Inn & Suites by Radisson, Richmond I-95 South, VA or DoubleTree by Hilton Richmond - Midlothian.
How far in advance should I book my Chesterfield County vacation?
Reserving your spot early with Expedia means one less thing to worry about. Most air carriers advertise tickets up to 12 months prior to departure dates. Typically, this is the cheapest time to book. If circumstances have left you booking late, last-minute deals to Chesterfield County will sometimes occur just weeks before departure.
What does an Expedia Chesterfield County travel package include?
Rental cars, hotels and flights, or any combination of them — the choice is all yours! Whether you're headed to Chesterfield County with the whole family or traveling by yourself, there's a package to suit your style and budget. Once you've made your booking, why not add on some tours or activities?
What should I know before booking a Chesterfield County travel package?
Whether it's relaxation or adventure you're after, a Chesterfield County vacation package lets you plan your escape your way. Plus, you'll get access to great discounts when you combine your accommodations with your flights and rental car. The more you bundle, the bigger the savings!
Can I choose my airline with a Chesterfield County Expedia vacation package?
With a vacation package, you're always in charge. Whether you'd prefer to fly to Chesterfield County in economy or business class, simply pick from the available airline options. Expedia has access to over 550 airline partners worldwide.
If I'm not able to travel, can I cancel my Chesterfield County vacation package?
Whether it's your flight or hotel, you can cancel or alter it. Locked in your Chesterfield County vacation package in the last 24 hours? You may be able to make changes or cancellations at no cost. For bookings made more than 24 hours ago, you may incur a fee from your hotel, airline or car rental company. For further information, look up our Customer Service Portal. We're here to help you every step of the way.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.