Chester Vacation Packages 2026 from $411

Chester flight + hotel vacation packages

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

OYO Palm Leaf Motel

$411

per person

May 28 - Jun 1

found 1 hour ago

Roundtrip flight included

Boston (BOS) to Richmond (RIC)

Free self parking is available and the hotel's front desk is staffed around-the-clock. WiFi in public areas is free. A safe deposit box is also provided.

The Colonies at Williamsburg

$840

per person

Jun 2 - Jun 9

found 1 day ago

Roundtrip non-stop flight included

Salt Lake City (SLC) 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.

Wingate by Wyndham Richmond Short Pump

Short Pump

$451

per person

May 28 - Jun 1

found 1 hour ago

Roundtrip flight included

Boston (BOS) to Richmond (RIC)

This hotel features an indoor pool and a 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.

Griffin Hotel, an official Colonial Williamsburg Hotel

Colonial Williamsburg

$745

per person

Jun 26 - Jun 29

found 11 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 Berkeley Hotel

Downtown Richmond

$547

per person

May 28 - Jun 1

found 1 hour ago

Roundtrip flight included

Boston (BOS) to Richmond (RIC)

This hotel features free WiFi in public areas, concierge services, and valet parking. Traveling for business? Take advantage of the 24-hour business center, express check-out, and conference space. A terrace, a computer station, and luggage storage are also on offer.

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

May 21 - May 22

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

SpringHill Suites Chester

12301 REDWATER CREEK ROAD Chester VA

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$127 total

May 10 - May 11

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

Apr 27 - Apr 28

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

Comfort Inn Chester - Richmond South

2100 W Hundred Rd Chester VA

Free Cancellation

$77 nightly

$90 total

Apr 28 - Apr 29

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

Hyatt Select Richmond/Chester

13148 Kingston Ave Chester VA

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$128 total

Apr 26 - Apr 27

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

Country Inn & Suites by Radisson, Chester, VA

2406 W Hundred Rd Chester VA

Free Cancellation

$99 nightly

$115 total

May 3 - May 4

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

Short Pump Town Center

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.

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 $411. 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.