Chester Vacation Packages 2026 from $558

Chester flight + hotel vacation packages

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

Kingsmill Resort

Kingsmill

$558

per person

Aug 13 - Aug 16

found 16 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) 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.

Holiday Inn Hotel & Suites Williamsburg-Historic Gateway by IHG

$591

per person

Jun 30 - Jul 3

found 4 hours ago

Roundtrip flight included

Houston (IAH) to Richmond (RIC)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Wedmore Place

$626

per person

Jun 30 - Jul 3

found 4 hours ago

Roundtrip flight included

Houston (IAH) to Richmond (RIC)

This boutique hotel features an attached winery, a full-service spa, and a restaurant. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference space. Enjoy the gym and free perks like continental breakfast and free self parking.

Club Wyndham Kingsgate

$631

per person

Jun 30 - Jul 3

found 4 hours ago

Roundtrip flight included

Houston (IAH) 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 playground. Enjoy the indoor pool and perks like free self parking and free WiFi.

Embassy Suites Williamsburg

$594

per person

Jun 30 - Jul 3

found 4 hours ago

Roundtrip flight included

Houston (IAH) to Richmond (RIC)

This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy free perks like buffet breakfast and free self parking.

Top Chester hotels deals

SpringHill Suites Chester

12301 REDWATER CREEK ROAD Chester VA

Free Cancellation

Reserve now, pay when you stay

$120 nightly

$140 total

Jun 11 - Jun 12

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 28 - Jun 29

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

Jun 7 - Jun 8

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

$127 nightly

$147 total

Jun 1 - Jun 2

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

$74 nightly

$86 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 21 - Jun 22

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

Kings Dominion

4.5/5(317 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.

Short Pump Town Center

4.5/5(472 reviews)

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.

Greater Richmond Convention Center

4/5(214 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 $558. 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.