Chesterfield Vacation Packages 2026 from $527

Chesterfield flight + hotel vacation packages

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

Westgate Historic Williamsburg Resort

Midtown

Save 100% on your flight

$527

per person

Jun 13 - Jun 17

found 1 day ago

Roundtrip flight included

New York (JFK) 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 Colonies at Williamsburg

Save 100% on your flight

$688

per person

Jul 6 - Jul 12

found 13 hours ago

Roundtrip non-stop flight included

New York (NYC) 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.

Griffin Hotel, an official Colonial Williamsburg Hotel

Colonial Williamsburg

$559

per person

Jun 13 - Jun 17

found 1 day ago

Roundtrip flight included

New York (JFK) 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.

Wedmore Place

Save 100% on your flight

$780

per person

Jul 6 - Jul 12

found 13 hours ago

Roundtrip non-stop flight included

New York (NYC) to Richmond (RIC)

This boutique hotel features an attached winery, a full-service spa, and a restaurant. 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.

Williamsburg Inn, an official Colonial Williamsburg Hotel

Colonial Williamsburg

Save 100% on your flight

$1,524

per person

Jun 13 - Jun 17

found 1 day ago

Roundtrip flight included

New York (JFK) to Richmond (RIC)

A full-service spa, 2 restaurants, and 6 outdoor tennis courts are all featured at this luxury hotel. You'll appreciate the indoor pool, bar/lounge, and concierge services.

Top Chesterfield hotels deals

Graduate by Hilton Richmond

301 West Franklin Street Richmond VA

Free Cancellation

Reserve now, pay when you stay

$147 nightly

$171 total

May 18 - May 19

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

$86 nightly

$100 total

Jun 1 - Jun 2

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

Omni Richmond Hotel

100 S 12th St Richmond VA

Free Cancellation

Reserve now, pay when you stay

$179 nightly

$208 total

May 31 - Jun 1

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

The Jefferson Hotel

101 West Franklin Street Richmond VA

Free Cancellation

Reserve now, pay when you stay

$295 nightly

$343 total

May 25 - May 26

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

$120 nightly

$140 total

Jun 1 - Jun 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

The Commonwealth

901 Bank St Richmond VA

Free Cancellation

Reserve now, pay when you stay

$159 nightly

$185 total

May 3 - May 4

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.

Magnolia Grange

You can browse the exhibits at Magnolia Grange, a museum with a storied past, during your travels to Chesterfield Court House. Amble around the area's riverfront or attend a sporting event.

Frequently asked questions

How much are vacation packages to Chesterfield?

Packages, which include flights and hotels in Chesterfield, start from as little as $527. 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.