Chester Vacation Packages 2026 from $702

Chester flight + hotel vacation packages

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

Wingate by Wyndham Richmond Short Pump

Short Pump

$702

per person

Jul 2 - Jul 6

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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

Colonial Williamsburg

$1,111

per person

Jul 15 - Jul 21

found 23 hours ago

Roundtrip flight included

Anchorage (ANC) 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.

Williamsburg Inn, an official Colonial Williamsburg Hotel

Colonial Williamsburg

$1,894

per person

Jul 15 - Jul 21

found 23 hours ago

Roundtrip flight included

Anchorage (ANC) to Richmond (RIC)

A full-service spa, 2 restaurants, and 6 outdoor tennis courts are all featured at this luxury hotel. You'll appreciate the indoor pool, bar/lounge, and concierge services.

Hilton Richmond Downtown

Downtown Richmond

$1,597

per person

Jul 15 - Jul 21

found 23 hours ago

Roundtrip flight included

Anchorage (ANC) 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.

The Commonwealth

Downtown Richmond

$837

per person

Jul 2 - Jul 6

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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 Chester hotels deals

SpringHill Suites Chester

12301 REDWATER CREEK ROAD Chester VA

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$127 total

May 31 - Jun 1

Total with taxes and fees

This hotel features an indoor pool and a 24-hour 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

Suburban Studios Chester

2403 W Hundred Rd Chester VA

Free Cancellation

Reserve now, pay when you stay

$67 nightly

$78 total

Jun 21 - Jun 22

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 free internet in public areas. There's a seasonal outdoor pool on site, and laundry facilities and free newspapers are also offered.

Pool

Pet friendly

Fairfield Inn By Marriott Richmond Chester

12400 Redwater Creek Rd Chester VA

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$116 total

May 25 - May 26

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the business center and free internet in public areas. There's a gym on site, and laundry facilities and free newspapers are also offered.

Breakfast included

Pet friendly

Hyatt Select Richmond/Chester

13148 Kingston Ave Chester VA

Free Cancellation

Reserve now, pay when you stay

$125 nightly

$145 total

May 25 - May 26

Total with taxes and fees

This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like self-serve breakfast and free self parking.

Pool

Breakfast included

Comfort Inn Chester - Richmond South

2100 W Hundred Rd Chester VA

Free Cancellation

$72 nightly

$83 total

May 31 - Jun 1

Total with taxes and fees

A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.

Pool

Breakfast included

Country Inn & Suites by Radisson, Chester, VA

2406 W Hundred Rd Chester VA

Free Cancellation

$97 nightly

$113 total

Jun 14 - Jun 15

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like self-serve breakfast and free self parking.

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

Short Pump Town Center

You can browse for souvenirs with a trip to Short Pump Town Center, a favorite shopping spot in Richmond. Attend a sporting event or simply enjoy the charming coffeehouses while you're in the area.

Kings Dominion

Bring the family to Kings Dominion and enjoy the excitement of this amusement park in Doswell. Experience the festivals or attend a sporting event in this family-friendly area.

G5KT01 Egyptian building historic college Richmond Virginia

Virginia Commonwealth University

Explore the campus of Virginia Commonwealth University during your stay in Richmond. Stroll along the area's riverfront or experience its great live music.

Frequently asked questions

How much are vacation packages to Chester?

Your travel fantasies can be realized in Chester from just $702. Our affordable package deals include flights and hotels, and they'll make your booking a cinch. The only thing you'll have to focus on is getting out there and having a great time.

How long should my Chester vacation be?

An average of 2 nights is how long most people spend checking out the delights of Chester. Not sure if that'll be enough time to squeeze in everything on your to-do list? Stay another night or two so you don't miss a thing.

Where can I get the best vacation package deals for Chester?

For the perfect Chester package deal, head straight to Travelocity. Take your pick of 400 airlines and 1,000,000 properties around the world to create your dream trip — the choice is all yours!

Why should I book my Chester vacation package with Travelocity?

Nothing beats the peace of mind knowing you've bagged the best deal in town — that's our Price Match Guarantee. Add to that our impressive range of magical destinations and 24/7 team of customer service professionals and you've got the blueprint for a stress-free vacation.

Will I save money on my Chester car rental if I bundle it with hotels and flights?

With a Chester vacation package, you can combine your hotel, flight and car bookings and save a whole lot. If you want to explore the best of this impressive area, why not make a beeline for White House? This popular attraction is 110 mi from Chester. With your own rental car, you'll be there in no time.

Which airport is best for Chester?

Chester has two major airports to pick from — Richmond Intl. Airport (RIC) (12 mi away from the city center) and Newport News - Williamsburg Intl. Airport (PHF) (55 mi away from central Chester).

What is there to do in Chester?

You'll sense a certain magic in the air as you stroll the streets of Chester. Iron Bridge Sports Park and The Lazy Daisy are just two renowned sights that make this city so special, so put them at the top of your itinerary.

Where should I stay when visiting Chester?

Many travelers choose to hit the hay at the Country Inn & Suites by Radisson, Chester, VA. It's a great base for your Chester vacation.