Chester Vacation Packages 2026 from $546

Chester flight + hotel vacation packages

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

Hilton Vacation Club The Historic Powhatan Williamsburg

$546

per person

May 13 - May 17

found 2 hours ago

Roundtrip non-stop flight included

San Antonio (SAT) to Richmond (RIC)

This smoke-free resort features 2 outdoor tennis courts, an outdoor pool, and a restaurant. There's fun for all ages with a free kid's club and mini golf, and supervised childcare is an added bonus. Enjoy the indoor pool and perks like free self parking and free WiFi.

Westgate Historic Williamsburg Resort

Midtown

Save 100% on your flight

$765

per person

May 13 - May 17

found 2 hours ago

Roundtrip non-stop flight included

San Antonio (SAT) to Richmond (RIC)

This hotel features a gym and a seasonal outdoor pool. There's fun for all ages with a children's club and mini golf, and families will appreciate the onsite laundry facilities. Enjoy the hot tub and perks like free self parking and free WiFi.

Westgate Williamsburg

Midtown

$981

per person

May 13 - May 17

found 2 hours ago

Roundtrip non-stop flight included

San Antonio (SAT) to Richmond (RIC)

This resort doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the 24-hour business center. The front desk is staffed around-the-clock and laundry facilities are on offer.

Holiday Inn Club Vacations Williamsburg Resort by IHG

$796

per person

May 13 - May 17

found 2 hours ago

Roundtrip non-stop flight included

San Antonio (SAT) 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.

Hotel Weyanoke

$764

per person

Apr 10 - Apr 12

found 1 day ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Richmond (RIC)

This smoke-free hotel features 2 restaurants, a bar/lounge, and a gym. Guests will appreciate free perks like free self parking and WiFi in public areas. A safe deposit box and concierge services are also provided.

Top Chester hotels deals

SpringHill Suites Chester

12301 REDWATER CREEK ROAD Chester VA

Free Cancellation

Reserve now, pay when you stay

$123 nightly

$143 total

Mar 1 - Mar 2

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

Candlewood Suites Chester Richmond by IHG

225 E Hundred Rd Chester VA

Free Cancellation

$116 nightly

$135 total

Feb 27 - Feb 28

Total with taxes and fees

Staff at the 24-hour front desk can provide around-the-clock assistance. Take advantage of the self parking.

Pet friendly

Parking available

Quality Inn Chester - South Richmond

12711 Old Stage Rd Chester VA

Free Cancellation

Reserve now, pay when you stay

$74 nightly

$86 total

Feb 22 - Feb 23

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. There's a 24-hour gym on site, and laundry facilities and free newspapers are also offered.

Breakfast included

Parking included

Suburban Studios Chester

2403 W Hundred Rd Chester VA

Free Cancellation

Reserve now, pay when you stay

$64 nightly

$74 total

Mar 22 - Mar 23

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.

Country Inn & Suites by Radisson, Chester, VA

2406 W Hundred Rd Chester VA

Free Cancellation

$92 nightly

$107 total

Feb 28 - Mar 1

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.

Hyatt Select Richmond/Chester

13148 Kingston Ave Chester VA

Free Cancellation

Reserve now, pay when you stay

$118 nightly

$137 total

Feb 23 - Feb 24

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

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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

4.5/5(464 reviews)

During your trip to Richmond, you can do some window-shopping at Short Pump Town Center. Attend a sporting event or simply enjoy the charming coffeehouses while you're in the area.

Kings Dominion

4.5/5(315 reviews)

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.

Greater Richmond Convention Center

4/5(209 reviews)

Learn about the events happening at Greater Richmond Convention Center during your trip to Richmond. Wander around the area's picturesque gardens 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 $546. 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.