Chester Vacation Packages 2026 from $341

Chester flight + hotel vacation packages

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

Hilton Vacation Club The Historic Powhatan Williamsburg

$341

per person

May 1 - May 4

found 22 hours ago

Roundtrip non-stop flight included

Boston (BOS) 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.

Griffin Hotel, an official Colonial Williamsburg Hotel

Colonial Williamsburg

Save 100% on your flight

$571

per person

May 1 - May 4

found 22 hours ago

Roundtrip non-stop flight included

Boston (BOS) 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.

The Colonies at Williamsburg

$386

per person

May 1 - May 4

found 22 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Richmond (RIC)

2 outdoor tennis courts, an indoor pool, and a lazy river are all featured at this smoke-free hotel. Bring the family and enjoy the free water park, children's pool, and playground. Enjoy the gym and perks like free self parking.

Wedmore Place

$529

per person

May 1 - May 4

found 22 hours ago

Roundtrip non-stop flight included

Boston (BOS) 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.

Hilton Vacation Club Greensprings Williamsburg

$381

per person

May 1 - May 4

found 22 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Richmond (RIC)

This resort features an outdoor pool and an indoor pool. There's fun for all ages with mini golf and a children's pool, and barbecue grills are available on site. Enjoy the gym and perks like free self parking and free WiFi.

Top Chester hotels deals

Suburban Studios Chester

2403 W Hundred Rd Chester VA

Free Cancellation

Reserve now, pay when you stay

$64 nightly

$74 total

Apr 20 - Apr 21

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

Country Inn & Suites by Radisson, Chester, VA

2406 W Hundred Rd Chester VA

Free Cancellation

$93 nightly

$108 total

Apr 5 - Apr 6

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.

Fairfield Inn By Marriott Richmond Chester

12400 Redwater Creek Rd Chester VA

Free Cancellation

Reserve now, pay when you stay

$107 nightly

$125 total

Mar 22 - Mar 23

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

Candlewood Suites Chester Richmond by IHG

225 E Hundred Rd Chester VA

$123 nightly

$143 total

Apr 3 - Apr 4

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

Air conditioning

Hampton Inn by Hilton Chester South

12610 Chestnut Hill Rd Chester VA

Free Cancellation

Reserve now, pay when you stay

$100 nightly

$116 total

Apr 5 - Apr 6

Total with taxes and fees

A gym, self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like buffet breakfast and WiFi in public areas. A business center, express check-in, and express check-out are also on offer.

Omni Richmond Hotel

100 S 12th St Richmond VA

Free Cancellation

Reserve now, pay when you stay

$169 nightly

$197 total

Mar 22 - Mar 23

Total with taxes and fees

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.

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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

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

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 $341. 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.