Chester Vacation Packages 2026 from $623

Chester flight + hotel vacation packages

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

King’s Creek Resort by Spinnaker

$623

per person

Aug 21 - Aug 24

just found

Roundtrip flight included

Minneapolis (MSP) to Richmond (RIC)

2 outdoor pools, 2 outdoor tennis courts, and an indoor pool are all featured at this luxury aparthotel. There's fun for all ages with mini golf and express theme park tickets, and barbecue grills are available on site. Enjoy the gym and perks like free self parking.

Holiday Inn Express Williamsbrg Busch Gardens Area by IHG

$1,063

per person

Aug 14 - Aug 21

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Richmond (RIC)

This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.

The Commonwealth

Downtown Richmond

$676

per person

Sep 16 - Sep 19

found 19 hours ago

Roundtrip 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.

Kingsmill Resort

Kingsmill

$1,403

per person

Aug 14 - Aug 21

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Richmond (RIC)

This smoke-free hotel features a golf course, a full-service spa, and a marina. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Bring the family and enjoy the lazy river, children's pool, and waterslide.

Omni Richmond Hotel

Downtown Richmond

$796

per person

Sep 16 - Sep 19

found 19 hours ago

Roundtrip flight included

Minneapolis (MSP) to Richmond (RIC)

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.

Top Chester hotels deals

Fairfield Inn By Marriott Richmond Chester

12400 Redwater Creek Rd Chester VA

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$114 total

Jul 12 - Jul 13

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

SpringHill Suites Chester

12301 REDWATER CREEK ROAD Chester VA

Free Cancellation

Reserve now, pay when you stay

$120 nightly

$140 total

Jul 16 - Jul 17

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

Aug 3 - Aug 4

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

Hyatt Select Richmond/Chester

13148 Kingston Ave Chester VA

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$128 total

Jul 12 - Jul 13

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

$79 nightly

$92 total

Aug 2 - Aug 3

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

Holiday Inn Express Chester by IHG

1911 W Hundred Rd Chester VA

Free Cancellation

$97 nightly

$113 total

Jul 12 - Jul 13

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the business center, express check-out, and conference space. There's a 24-hour gym on site, and a 24-hour front desk and dry cleaning are also provided.

Breakfast included

Parking 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.

Stay near popular Chester attractions

Henricus Historical Park

8.0/10 (63 reviews)

Explore the great outdoors at Henricus Historical Park, a lovely green space in Chester. You can attend a sporting event while in the area.

See properties

Frequently asked questions

How much are vacation packages to Chester?

Your travel fantasies can be realized in Chester from just $623. 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.