Chester Vacation Packages 2026 from $463

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

$463

per person

Jan 4 - Jan 8

just found

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 for business? Take advantage of the express check-out, laundry service, and conference space. You'll also find 6 outdoor tennis courts and an indoor pool.

Westgate Historic Williamsburg Resort

Midtown

Save 100% on your flight

$471

per person

Jan 4 - Jan 8

just found

Roundtrip non-stop flight included

Boston (BOS) 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.

Wedmore Place

$752

per person

Dec 3 - Dec 7

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Richmond (RIC)

An attached winery and a restaurant are featured at this boutique hotel. 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.

The Commonwealth

Downtown Richmond

$876

per person

Jan 6 - Jan 10

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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.

Club Wyndham Governor’s Green

$849

per person

Dec 20 - Dec 24

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Richmond (RIC)

2 outdoor pools, 3 hot tubs, and an indoor pool are all featured at this smoke-free hotel. There's fun for all ages with mini golf and a children's pool, and families will appreciate the picnic area. Enjoy the gym and perks like free self parking and free WiFi.

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

Oct 29 - Oct 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

$98 nightly

$114 total

Oct 18 - Oct 19

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

$94 nightly

$109 total

Oct 18 - Oct 19

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

Courtyard by Marriott Richmond Chester

2001 W Hundred Rd Chester VA

Free Cancellation

Reserve now, pay when you stay

$116 nightly

$135 total

Oct 25 - Oct 26

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 and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Pool

Parking included

Holiday Inn Express Chester by IHG

1911 W Hundred Rd Chester VA

Free Cancellation

$100 nightly

$116 total

Oct 18 - Oct 19

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

Country Inn & Suites by Radisson, Chester, VA

2406 W Hundred Rd Chester VA

Free Cancellation

$83 nightly

$97 total

Nov 8 - Nov 9

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.

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 $463. 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.