Deals on vacations and trips to Chesterfield

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Chesterfield flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Westgate Historic Williamsburg Resort

Westgate Historic Williamsburg Resort

3.5 out of 5
Save 100% on your flight
per person
Aug 12 - Aug 16
found 22 hours ago
Roundtrip flight included
New York (NYC) 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.
Williamsburg Inn, an official Colonial Williamsburg Hotel

Williamsburg Inn, an official Colonial Williamsburg Hotel

5 out of 5
Colonial Williamsburg
Save 100% on your flight
per person
Aug 21 - Aug 26
found 24 hours ago
Roundtrip flight included
New York (NYC) to Richmond (RIC)
A full-service spa, 3 restaurants, and 6 outdoor tennis courts are all featured at this luxury hotel. You'll appreciate the indoor pool, bar/lounge, and concierge services.
Linden Row Inn

Linden Row Inn

3 out of 5
Downtown Richmond
Save 100% on your flight
per person
Aug 20 - Aug 25
found 10 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
Free WiFi in public areas, a terrace, and a garden are available at this hotel. A picnic area, express check-out, and luggage storage are also on offer.
Virginia Crossings Hotel, Tapestry Collection by Hilton

Virginia Crossings Hotel, Tapestry Collection by Hilton

3.5 out of 5
Save 100% on your flight
per person
Aug 12 - Aug 16
found 22 hours ago
Roundtrip flight included
New York (NYC) to Richmond (RIC)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. Enjoy the hot tub and conveniences like a 24-hour front desk and laundry facilities.
The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Save 100% on your flight
per person
Aug 20 - Aug 25
found 10 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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

Regency Inn Richmond

Regency Inn Richmond

2 out of 5
1500 Eastridge Road, Richmond, VA
Free Cancellation
Reserve now, pay when you stay
$62 nightly
The price is $73 total per night
$73 total
Jul 3 - Jul 4
Total includes 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.
The Commonwealth

The Commonwealth

4 out of 5
901 Bank St, Richmond, VA
Free Cancellation
Reserve now, pay when you stay
$151 nightly
The price is $176 total per night
$176 total
Jun 15 - Jun 16
Total includes 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.
Omni Richmond Hotel

Omni Richmond Hotel

4 out of 5
100 S 12th St, Richmond, VA
Free Cancellation
Reserve now, pay when you stay
$151 nightly
The price is $176 total per night
$176 total
Jun 29 - Jun 30
Total includes 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.
Drury Plaza Hotel Richmond

Drury Plaza Hotel Richmond

3 out of 5
11049 West Broad St, Glen Allen, VA
Free Cancellation
Reserve now, pay when you stay
$126 nightly
The price is $147 total per night
$147 total
Jun 29 - Jun 30
Total includes 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.
Wingate by Wyndham Richmond Short Pump

Wingate by Wyndham Richmond Short Pump

2.5 out of 5
13991 N Gayton Rd, Richmond, VA
Free Cancellation
Reserve now, pay when you stay
$105 nightly
The price is $123 total per night
$123 total
Jun 15 - Jun 16
Total includes taxes and fees
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 buffet breakfast and free self parking.
The Jefferson Hotel

The Jefferson Hotel

5 out of 5
101 West Franklin Street, Richmond, VA
Free Cancellation
Reserve now, pay when you stay
$285 nightly
The price is $331 total per night
$331 total
Jul 1 - Jul 2
Total includes 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.
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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

While hiking with my wife in Pocahontas State Park in Virginia we came across this doll left on the trail. I thought it would make for a cool photo.

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.

Pocahontas State Park

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.

Pocahontas State Park Museum

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.

Castlewood

Frequently asked questions

How much are vacation packages to Chesterfield?
Packages, which include flights and hotels in Chesterfield, start from as little as $295. 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.

Photos of local treasures

Browse Chesterfield vacation photos for more inspiration

Photo by Nick Pagano
Photo by Nick Pagano