Deals on vacations and trips to Chesterfield

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Chesterfield flight + hotel vacation packages

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A house full of steel balls and games

A house full of steel balls and games

2.5 out of 5
Dumbarton
Save 100% on your flight
Price was $381, price is now $245 per person
$245
per person
Oct 23 - Oct 27
found 16 hours ago
Roundtrip flight included
Tampa (TPA) to Richmond (RIC)
This bed & breakfast doesn't skimp on freebies - guests receive free breakfast, free WiFi, and free self parking. Families will appreciate the arcade/game room and barbecue grills. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls.
Hilton Richmond Downtown

Hilton Richmond Downtown

4 out of 5
Downtown Richmond
Save 100% on your flight
Price was $900, price is now $606 per person
$606
per person
Oct 23 - Oct 27
found 16 hours ago
Roundtrip flight included
Tampa (TPA) to Richmond (RIC)
This traditional hotel includes 3 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities are also provided.
Club Wyndham Kingsgate

Club Wyndham Kingsgate

3 out of 5
Price was $393, price is now $265 per person
$265
per person
Nov 3 - Nov 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
This Colonial resort features 2 outdoor tennis courts, an outdoor pool, and a restaurant. Bring the family and enjoy the mini golf, children's pool, and arcade/game room. Enjoy the indoor pool and perks like free self parking and free WiFi.
Griffin Hotel, an official Colonial Williamsburg Hotel

Griffin Hotel, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
Save 100% on your flight
Price was $429, price is now $290 per person
$290
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.
The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
Save 100% on your flight
Price was $474, price is now $323 per person
$323
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

Omni Richmond Hotel

Omni Richmond Hotel

4 out of 5
100 S 12th St, Richmond, VA
Free Cancellation
Reserve now, pay when you stay
$159 nightly
The price is $185 total per night
$185 total
Sep 1 - Sep 2
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

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
Sep 1 - Sep 2
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

Drury Plaza Hotel Richmond

3 out of 5
11049 West Broad St, Glen Allen, VA
Free Cancellation
Reserve now, pay when you stay
$112 nightly
The price is $131 total per night
$131 total
Aug 31 - Sep 1
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
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
$102 nightly
The price is $119 total per night
$119 total
Sep 2 - Sep 3
Total with 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.
Pool
Breakfast included
Studio 6 Richmond, VA - Airport

Studio 6 Richmond, VA - Airport

2 out of 5
580 Trampton Road, Sandston, VA
Free Cancellation
Reserve now, pay when you stay
$76 nightly
The price is $88 total per night
$88 total
Sep 8 - Sep 9
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
Graduate by Hilton Richmond

Graduate by Hilton Richmond

4 out of 5
301 West Franklin Street, Richmond, VA
Free Cancellation
Reserve now, pay when you stay
$152 nightly
The price is $177 total per night
$177 total
Sep 3 - Sep 4
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
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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

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

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.

Castlewood

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

Frequently asked questions

How much are vacation packages to Chesterfield?
Packages, which include flights and hotels in Chesterfield, start from as little as $245. 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