Chesterfield Vacation Packages 2026 from $497

Chesterfield flight + hotel vacation packages

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

Patriots Inn

$497

per person

Jun 3 - Jun 10

found 11 hours ago

Roundtrip flight included

Dallas (DFW) to Richmond (RIC)

This motel features an outdoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and perks like free self parking.

The Colonies at Williamsburg

Save 100% on your flight

$619

per person

Jun 3 - Jun 10

found 11 hours ago

Roundtrip flight included

Dallas (DFW) to Richmond (RIC)

2 outdoor tennis courts, an indoor pool, and a lazy river are all featured at this smoke-free hotel. Bring the family and enjoy the free water park, children's pool, and playground. Enjoy the gym and perks like free self parking.

Hilton Vacation Club The Historic Powhatan Williamsburg

$513

per person

Jun 3 - Jun 10

found 11 hours ago

Roundtrip flight included

Dallas (DFW) to Richmond (RIC)

This smoke-free resort features 2 outdoor tennis courts, an outdoor pool, and a restaurant. There's fun for all ages with a free kid's club and mini golf, and supervised childcare is an added bonus. Enjoy the indoor pool and perks like free self parking and free WiFi.

Griffin Hotel, an official Colonial Williamsburg Hotel

Colonial Williamsburg

$512

per person

Jun 5 - Jun 7

found 14 hours ago

Roundtrip non-stop flight included

Providence (PVD) to Richmond (RIC)

A golf course, a full-service spa, and 3 outdoor pools are all featured at this smoke-free hotel. Traveling on business? Take advantage of the express check-out and WiFi in public areas. You'll also find 6 outdoor tennis courts and an indoor pool.

Linden Row Inn

Downtown Richmond

Save 100% on your flight

$852

per person

Jun 3 - Jun 10

found 11 hours ago

Roundtrip flight included

Dallas (DFW) to Richmond (RIC)

Free WiFi in public areas, a terrace, and a garden are available at this hotel. A picnic area, express check-out, and luggage storage are also on offer.

Top Chesterfield hotels deals

Omni Richmond Hotel

100 S 12th St Richmond VA

Free Cancellation

Reserve now, pay when you stay

$181 nightly

$210 total

Apr 26 - Apr 27

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and wedding services.

Pool

Pet friendly

Graduate by Hilton Richmond

301 West Franklin Street Richmond VA

Free Cancellation

Reserve now, pay when you stay

$147 nightly

$171 total

Apr 30 - May 1

Total with taxes and fees

A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. There's a rooftop terrace on site, and a 24-hour front desk and a terrace are also provided.

Pet friendly

Free WiFi

Studio 6 Richmond Airport

580 Trampton Road Sandston VA

Free Cancellation

Reserve now, pay when you stay

$87 nightly

$101 total

Apr 22 - Apr 23

Total with taxes and fees

A gym is featured at this motel, along with laundry facilities. Staff at the 24-hour front desk can provide around-the-clock assistance.

Pet friendly

Free WiFi

The Jefferson Hotel

101 West Franklin Street Richmond VA

Free Cancellation

Reserve now, pay when you stay

$315 nightly

$366 total

May 3 - May 4

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Unwind with a drink at one of the 2 bars/lounges and enjoy perks like a free area shuttle.

Pool

Spa

Drury Plaza Hotel Richmond

11049 West Broad St Glen Allen VA

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$138 total

Apr 26 - Apr 27

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the indoor pool and free perks like buffet breakfast and free self parking.

Pool

Hot Tub

Red Roof Inn Richmond South

4350 Commerce Rd Richmond VA

Free Cancellation

Reserve now, pay when you stay

$73 nightly

$85 total

May 1 - May 2

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, express check-out, and concierge services are also on offer.

Pet friendly

Parking included

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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.

Popular places to visit

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.

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.

Civilian Conservation Corps Museum

You can spend an afternoon browsing the exhibits at Civilian Conservation Corps Museum in Chesterfield. Take in the live music in this family-friendly area.

Frequently asked questions

How much are vacation packages to Chesterfield?

Packages, which include flights and hotels in Chesterfield, start from as little as $497. Make your travel dreams come true and secure your dream vacation with Travelocity today.

Where can I get the best vacation package deals for Chesterfield?

Travelocity will be able to help you snap up a great Chesterfield package deal. With no less than 400 partner airlines and 1,000,000 properties across the world, you're sure to find one that works for you.

Why should I book my Chesterfield vacation package with Travelocity?

Because we believe in creating special travel experiences. From hotels and flights to car rentals and activities, our packages make it a breeze to save. Our support team is on hand 24/7 to make sure you'll never roam alone. We also offer a Price Match Guarantee, so you can lock in your trip knowing you've scored the best deal around.

Can I save on my Chesterfield car rental if I combine it with my hotel or flight?

Sure can — combine your hotel, flight and car into a Chesterfield vacation package and you'll save plenty. With so much to see and do in Chesterfield, that rental vehicle will make it easy to explore. Once you've slid into the driver's seat, crank up the music and head to White House, a top attraction roughly 110 mi from Chesterfield.

Which airport is best for Chesterfield?

There are two choices for landing at Chesterfield, the first being Richmond Intl. Airport (RIC). It's roughly 13 mi from the center of the city, while Newport News - Williamsburg Intl. Airport (PHF) is 60 mi away from central Chesterfield.

What is there to do in Chesterfield?

While veering off the tourist trail is rewarding, you shouldn't miss the popular attractions that make a destination famous. Pocahontas State Park and Castlewood are a couple of them in Chesterfield.

Where should I stay when visiting Chesterfield?

Many visitors spend their nights at the Private bedroom and bath!. It's an excellent base for your Chesterfield vacation.