Chesterfield Vacation Packages 2025/2026 from $367

Chesterfield flight + hotel vacation packages

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

The Berkeley Hotel

Downtown Richmond

Save 100% on your flight

$367

per person

Jan 22 - Jan 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Richmond (RIC)

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

The Colonies at Williamsburg

Save 100% on your flight

$426

per person

Jan 5 - Jan 12

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.

Kingsmill Resort

Kingsmill

Save 100% on your flight

$453

per person

Jan 5 - Jan 12

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Bluegreen Vacations Patrick Henry Square, an Ascend Collection Resort

Save 100% on your flight

$414

per person

Jan 5 - Jan 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Richmond (RIC)

This hotel features an indoor pool and a 24-hour gym. Families will appreciate the arcade/game room and onsite laundry facilities. Guests will appreciate free perks like free self parking and WiFi in public areas.

The Commonwealth

Downtown Richmond

Save 100% on your flight

$462

per person

Jan 22 - Jan 26

found 1 day ago

Roundtrip 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.

Top Chesterfield hotels deals

The Jefferson Hotel

101 West Franklin Street Richmond VA

Free Cancellation

Reserve now, pay when you stay

$365 nightly

$424 total

Dec 29 - Dec 30

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

Free Cancellation

Reserve now, pay when you stay

$169 nightly

$197 total

Dec 7 - Dec 8

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 4 - Dec 5

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

Regency Inn Richmond

1500 Eastridge Road Richmond VA

Free Cancellation

Reserve now, pay when you stay

$60 nightly

$70 total

Dec 1 - Dec 2

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

Graduate by Hilton Richmond

301 West Franklin Street Richmond VA

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$152 total

Dec 7 - Dec 8

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

Hyatt Place Richmond Airport

4401 S Laburnum Avenue Richmond VA

Free Cancellation

Reserve now, pay when you stay

$125 nightly

$145 total

Dec 2 - Dec 3

Total with taxes and fees

A 24-hour gym, self parking, and laundry facilities are featured at this hotel. Guests will appreciate freebies like buffet breakfast, WiFi in public areas, and a roundtrip airport shuttle. A 24-hour business center, a grocery/convenience store, and a lobby fireplace are also on offer.

Breakfast included

Free airport shuttle

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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

4/5(29 reviews)

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

Castlewood

4/5(1 review)

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 $367. 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.