Chesterfield Vacation Packages 2026 from $715

Chesterfield flight + hotel vacation packages

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

King’s Creek Resort by Spinnaker

$715

per person

Mar 18 - Mar 22

found 11 hours ago

Roundtrip non-stop flight included

Houston (IAH) to Richmond (RIC)

2 outdoor pools, 2 outdoor tennis courts, and an indoor pool are all featured at this luxury condo resort. There's fun for all ages with mini golf and express theme park tickets, and barbecue grills are available on site. Enjoy the gym and perks like free self parking.

Holiday Inn Club Vacations Williamsburg Resort by IHG

$770

per person

Mar 18 - Mar 22

found 11 hours ago

Roundtrip non-stop flight included

Houston (IAH) to Richmond (RIC)

This smoke-free resort features 2 outdoor pools, an indoor pool, and a restaurant. Bring the family and enjoy the free kid's club, bowling alley, and kid-friendly dining. Business travelers can take advantage of the business center.

Kingsmill Resort

Kingsmill

$754

per person

Mar 18 - Mar 22

found 11 hours ago

Roundtrip non-stop flight included

Houston (IAH) to Richmond (RIC)

This smoke-free hotel features a golf course, a full-service spa, and a marina. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Bring the family and enjoy the lazy river, children's pool, and waterslide.

Holiday Inn Express Williamsbrg Busch Gardens Area by IHG

$758

per person

Mar 18 - Mar 22

found 11 hours ago

Roundtrip non-stop flight included

Houston (IAH) to Richmond (RIC)

This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.

Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

$723

per person

Mar 18 - Mar 22

found 11 hours ago

Roundtrip non-stop flight included

Houston (IAH) to Richmond (RIC)

This hotel features a gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room. Guests will appreciate free perks like free self parking and WiFi in public areas.

Top Chesterfield hotels deals

The Jefferson Hotel

101 West Franklin Street Richmond VA

Free Cancellation

Reserve now, pay when you stay

$295 nightly

$343 total

Jan 6 - Jan 7, 2026

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

Regency Inn Richmond

1500 Eastridge Road Richmond VA

Free Cancellation

Reserve now, pay when you stay

$62 nightly

$73 total

Dec 27 - Dec 28

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the business center and onsite conference space. A restaurant and free parking are also offered on site.

Pet friendly

Parking included

Omni Richmond Hotel

100 S 12th St Richmond VA

Free Cancellation

Reserve now, pay when you stay

$152 nightly

$177 total

Jan 4 - Jan 5, 2026

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

Drury Plaza Hotel Richmond

11049 West Broad St Glen Allen VA

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$128 total

Dec 31 - Jan 1, 2026

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

Graduate by Hilton Richmond

301 West Franklin Street Richmond VA

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$152 total

Jan 4 - Jan 5, 2026

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

The Commonwealth

901 Bank St Richmond VA

Free Cancellation

Reserve now, pay when you stay

$160 nightly

$187 total

Dec 28 - Dec 29

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A snack bar/deli, express check-out, and a computer station are also on offer.

Pet friendly

Free WiFi

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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.

Pocahontas State Park Museum

You can spend an afternoon browsing the exhibits at Pocahontas State Park 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 $715. 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.