Chesterfield Vacation Packages 2026 from $268

Chesterfield flight + hotel vacation packages

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

Wingate by Wyndham Richmond Short Pump

Short Pump

$268

per person

Dec 5 - Dec 8

found 22 hours ago

Roundtrip flight included

Tampa (TPA) to Richmond (RIC)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.

Westgate Historic Williamsburg Resort

Midtown

$895

per person

Dec 19 - Dec 23

found 1 day ago

Roundtrip non-stop flight included

Oakland (OAK) to Richmond (RIC)

This hotel features a gym and a seasonal outdoor pool. There's fun for all ages with a children's club and mini golf, and families will appreciate the onsite laundry facilities. Enjoy the hot tub and perks like free self parking and free WiFi.

The Commonwealth

Downtown Richmond

$814

per person

Dec 1 - Dec 7

found 2 hours ago

Roundtrip non-stop flight included

Boston (BOS) 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

$1,015

per person

Dec 19 - Dec 23

found 1 day ago

Roundtrip non-stop flight included

Oakland (OAK) 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.

Club Wyndham Governor’s Green

$1,030

per person

Dec 19 - Dec 23

found 1 day ago

Roundtrip non-stop flight included

Oakland (OAK) 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

Comfort Suites At Virginia Center Commons

10601 Telegraph Rd Glen Allen VA

Free Cancellation

$88 nightly

$103 total

Nov 17 - Nov 18

Total with taxes and fees

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

Pool

Hot Tub

Holiday Inn & Suites Richmond West End

8008 W. Broad St Richmond VA

Free Cancellation

$103 nightly

$120 total

Nov 25 - Nov 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

Free Cancellation

Reserve now, pay when you stay

$315 nightly

$366 total

Nov 8 - Nov 9

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

Graduate by Hilton Richmond

301 West Franklin Street Richmond VA

Free Cancellation

Reserve now, pay when you stay

$147 nightly

$171 total

Nov 2 - Nov 3

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.

Drury Plaza Hotel Richmond

11049 West Broad St Glen Allen VA

Free Cancellation

Reserve now, pay when you stay

$115 nightly

$134 total

Nov 8 - Nov 9

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

Omni Richmond Hotel

100 S 12th St Richmond VA

Free Cancellation

Reserve now, pay when you stay

$170 nightly

$198 total

Nov 22 - Nov 23

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.

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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 $268. 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.