Chester Vacation Packages 2026 from $552

Chester flight + hotel vacation packages

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

Griffin Hotel, an official Colonial Williamsburg Hotel

Colonial Williamsburg

$552

per person

Mar 1 - Mar 5

found 18 hours ago

Roundtrip non-stop flight included

Grand Rapids (GRR) 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.

Linden Row Inn

Downtown Richmond

$788

per person

Mar 26 - Mar 29

found 21 hours ago

Roundtrip non-stop flight included

Jacksonville (JAX) to Richmond (RIC)

Free WiFi in public areas, a terrace, and a garden are available at this hotel. A picnic area, express check-out, and luggage storage are also on offer.

Hilton Richmond Downtown

Downtown Richmond

$730

per person

Mar 26 - Mar 29

found 21 hours ago

Roundtrip non-stop flight included

Jacksonville (JAX) 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.

Williamsburg Inn, an official Colonial Williamsburg Hotel

Colonial Williamsburg

$1,259

per person

Mar 5 - Mar 8

found 20 hours ago

Roundtrip non-stop flight included

Jacksonville (JAX) 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.

Graduate by Hilton Richmond

Downtown Richmond

$703

per person

Mar 26 - Mar 29

found 21 hours ago

Roundtrip non-stop flight included

Jacksonville (JAX) to Richmond (RIC)

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.

Top Chester hotels deals

SpringHill Suites Chester

12301 REDWATER CREEK ROAD Chester VA

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$138 total

Jan 29 - Jan 30

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

Fairfield Inn By Marriott Richmond Chester

12400 Redwater Creek Rd Chester VA

Free Cancellation

Reserve now, pay when you stay

$107 nightly

$125 total

Jan 26 - Jan 27

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

Suburban Studios Chester

2403 W Hundred Rd Chester VA

Free Cancellation

Reserve now, pay when you stay

$68 nightly

$78 total

Jan 27 - Jan 28

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

Quality Inn Chester - South Richmond

12711 Old Stage Rd Chester VA

Free Cancellation

Reserve now, pay when you stay

$74 nightly

$86 total

Jan 22 - Jan 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

Candlewood Suites Chester Richmond by IHG

225 E Hundred Rd Chester VA

$103 nightly

$120 total

Feb 1 - Feb 2

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

Country Inn & Suites by Radisson, Chester, VA

2406 W Hundred Rd Chester VA

Free Cancellation

$90 nightly

$104 total

Feb 15 - Feb 16

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

Don't see what you're looking for?

See all available properties in Chester

View all properties

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.

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.

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.

Frequently asked questions

How much are vacation packages to Chester?

Your travel fantasies can be realized in Chester from just $552. 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.