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.
Wingate by Wyndham Richmond Short Pump

Wingate by Wyndham Richmond Short Pump

2.5 out of 5
Short Pump
Save 100% on your flight
per person
Sep 13 - Sep 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
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.
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
per person
Sep 13 - Sep 19
found 4 hours 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.
Club Wyndham Kingsgate

Club Wyndham Kingsgate

3 out of 5
Save 100% on your flight
per person
Sep 13 - Sep 19
found 4 hours 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.
The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
Save 100% on your flight
per person
Sep 13 - Sep 19
found 4 hours 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.
Landing Apartments near Virginia Union University

Landing Apartments near Virginia Union University

3.5 out of 5
Save 100% on your flight
per person
Sep 13 - Sep 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
This aparthotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A virtual front desk are provided for your convenience.

Top Chesterfield hotels deals

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
Aug 17 - Aug 18
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.
Pool
Spa
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 1 - Sep 2
Total includes 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

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
Aug 24 - Aug 25
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.
Pool
Pet friendly
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
Aug 24 - Aug 25
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.
Pool
Breakfast included
Hilton Richmond Downtown

Hilton Richmond Downtown

4 out of 5
501 E Broad St, Richmond, VA
Free Cancellation
Reserve now, pay when you stay
$152 nightly
The price is $177 total per night
$177 total
Aug 17 - Aug 18
Total includes taxes and fees
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.
Pool
Pet friendly
Best Western Premier Richmond City Gateway

Best Western Premier Richmond City Gateway

3 out of 5
4303 Commerce Road, Richmond, VA
Free Cancellation
Reserve now, pay when you stay
$90 nightly
The price is $105 total per night
$105 total
Sep 1 - Sep 2
Total includes 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
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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

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

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 $425. 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