Chesterfield Vacation Packages 2026 from $391

Chesterfield flight + hotel vacation packages

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

Wedmore Place

$391

per person

Dec 1 - Dec 4

found 22 hours ago

Roundtrip flight included

Orlando (MCO) to Richmond (RIC)

An attached winery and a restaurant are featured at this boutique hotel. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference space. Enjoy the gym and free perks like continental breakfast and free self parking.

The Commonwealth

Downtown Richmond

$712

per person

Dec 15 - Dec 18

found 2 hours ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Richmond (RIC)

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.

Kingsmill Resort

Kingsmill

$659

per person

Dec 11 - Dec 14

found 1 hour ago

Roundtrip flight included

Dallas (DFW) 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.

The Colonies at Williamsburg

$581

per person

Dec 11 - Dec 14

found 1 hour 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.

Club Wyndham Governor’s Green

$700

per person

Dec 11 - Dec 14

found 1 hour ago

Roundtrip flight included

Dallas (DFW) to Richmond (RIC)

2 outdoor pools, 3 hot tubs, and an indoor pool are all featured at this smoke-free hotel. There's fun for all ages with mini golf and a children's pool, and families will appreciate the picnic area. Enjoy the gym and perks like free self parking and free WiFi.

Top Chesterfield hotels deals

Graduate by Hilton Richmond

301 West Franklin Street Richmond VA

$147 nightly

$171 total

Oct 4 - Oct 5

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

Holiday Inn & Suites Richmond West End

8008 W. Broad St Richmond VA

Free Cancellation

$103 nightly

$120 total

Oct 25 - Oct 26

Total with taxes and fees

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

Pool

Parking included

The Jefferson Hotel

101 West Franklin Street Richmond VA

$315 nightly

$366 total

Oct 4 - Oct 5

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

Omni Richmond Hotel

100 S 12th St Richmond VA

$189 nightly

$220 total

Oct 4 - Oct 5

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

$128 nightly

$149 total

Oct 1 - Oct 2

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

$66 nightly

$76 total

Sep 30 - Oct 1

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.

Stay near popular Chesterfield attractions

Pocahontas State Park

8.4/10 (31 reviews)

You can take time to visit Pocahontas State Park during your travels to Chesterfield. Attend a sporting event in this family-friendly area.

See properties

Frequently asked questions

How much are vacation packages to Chesterfield?

Packages, which include flights and hotels in Chesterfield, start from as little as $391. 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.