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.
The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was $663, price is now $564 per person
$564
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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.
The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
Price was $739, price is now $619 per person
$619
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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.
Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

3.5 out of 5
Price was $702, price is now $592 per person
$592
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Richmond (RIC)
This hotel features a gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room. Guests will appreciate free perks like free self parking and WiFi in public areas.
Holiday Inn Club Vacations Williamsburg Resort by IHG

Holiday Inn Club Vacations Williamsburg Resort by IHG

3.5 out of 5
Price was $692, price is now $594 per person
$594
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Richmond (RIC)
This smoke-free resort features 2 outdoor pools, an indoor pool, and a restaurant. Bring the family and enjoy the free kid's club, bowling alley, and kid-friendly dining. Business travelers can take advantage of the business center.
Club Wyndham Kingsgate

Club Wyndham Kingsgate

3 out of 5
Price was $702, price is now $603 per person
$603
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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.

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
$169 nightly
The price is $197 total per night
$197 total
Dec 21 - Dec 22
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
$295 nightly
The price is $343 total per night
$343 total
Jan 4 - Jan 5, 2026
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
$110 nightly
The price is $128 total per night
$128 total
Dec 21 - Dec 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
Regency Inn Richmond

Regency Inn Richmond

2 out of 5
1500 Eastridge Road Richmond VA
Free Cancellation
Reserve now, pay when you stay
$58 nightly
The price is $68 total per night
$68 total
Dec 19 - Dec 20
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

Graduate by Hilton Richmond

4 out of 5
301 West Franklin Street Richmond VA
Free Cancellation
Reserve now, pay when you stay
$130 nightly
The price is $152 total per night
$152 total
Dec 21 - Dec 22
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
The Commonwealth

The Commonwealth

4 out of 5
901 Bank St Richmond VA
Free Cancellation
Reserve now, pay when you stay
$164 nightly
The price is $191 total per night
$191 total
Dec 21 - Dec 22
Total with 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.
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

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 $564. 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

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