Chesterfield Vacation Packages 2025/2026 from $270

Chesterfield flight + hotel vacation packages

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

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Colonial Williamsburg

$270

per person

Nov 3 - Nov 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Richmond (RIC)

Free water park access and an outdoor pool are 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 onsite laundry facilities. Enjoy the gym and free perks like continental breakfast and free self parking.

Griffin Hotel, an official Colonial Williamsburg Hotel

Colonial Williamsburg

$322

per person

Nov 3 - Nov 6

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Graduate by Hilton Richmond

Downtown Richmond

$382

per person

Nov 3 - Nov 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Richmond (RIC)

This hotel features 2 restaurants and a 24-hour gym. 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.

King’s Creek Resort by Spinnaker

$728

per person

Oct 17 - Oct 22

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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.

The Colonies at Williamsburg

$359

per person

Nov 3 - Nov 6

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Top Chesterfield hotels deals

Graduate by Hilton Richmond

301 West Franklin Street, Richmond, VA

Free Cancellation

Reserve now, pay when you stay

$169 nightly

$197 total

Sep 23 - Sep 24

Total with taxes and fees

This hotel features 2 restaurants and a 24-hour gym. 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

Omni Richmond Hotel

100 S 12th St, Richmond, VA

Free Cancellation

Reserve now, pay when you stay

$159 nightly

$185 total

Sep 28 - Sep 29

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

$305 nightly

$355 total

Sep 30 - Oct 1

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

$112 nightly

$131 total

Sep 21 - Sep 22

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

Best Western Premier Richmond City Gateway

4303 Commerce Road, Richmond, VA

Free Cancellation

Reserve now, pay when you stay

$90 nightly

$105 total

Sep 28 - Sep 29

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Enjoy the seasonal outdoor pool and free perks like full breakfast and free self parking. Free parking, a 24-hour business center, and a coffee shop are also offered.

Pool

Breakfast included

Studio 6 Richmond-Airport

580 Trampton Road, Sandston, VA

Free Cancellation

Reserve now, pay when you stay

$78 nightly

$91 total

Oct 6 - Oct 7

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

Don't see what you're looking for?

See all available properties in Chesterfield

View all properties

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.

Frequently asked questions

How much are vacation packages to Chesterfield?

Packages, which include flights and hotels in Chesterfield, start from as little as $270. 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.