Chester Vacation Packages 2025/2026 from $301

Chester flight + hotel vacation packages

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

A house full of steel balls and games

Dumbarton

per person

Sep 4 - Sep 8

found 10 hours ago

Roundtrip flight included

Chicago (ORD) to Richmond (RIC)

This bed & breakfast doesn't skimp on freebies - guests receive free breakfast, free WiFi, and free self parking. Families will appreciate the arcade/game room and barbecue grills. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls.

The Commonwealth

Downtown Richmond

Save 100% on your flight

per person

Aug 20 - Aug 25

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) 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.

Barsala At Sphere Apartments

Save 100% on your flight

per person

Aug 20 - Aug 25

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Richmond (RIC)

This aparthotel includes free WiFi in public areas and a virtual front desk. Take advantage of the self parking.

Linden Row Inn

Downtown Richmond

Save 100% on your flight

per person

Sep 25 - Sep 28

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) 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.

The Berkeley Hotel

Downtown Richmond

Save 100% on your flight

per person

Aug 20 - Aug 25

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Richmond (RIC)

A restaurant and a bar/lounge are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A terrace, express check-out, and a computer station are also on offer.

Top Chester hotels deals

Red Roof Inn Chester

2405 W Hundred Rd, Chester, VA

Free Cancellation

Reserve now, pay when you stay

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This hotel features free WiFi in public areas, laundry facilities, and free self parking. Free continental breakfast is served. Staff at the 24-hour front desk can provide around-the-clock assistance.

Breakfast included

Pet friendly

Country Inn & Suites by Radisson, Chester, VA

2406 W Hundred Rd, Chester, VA

Free Cancellation

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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

Comfort Inn Chester - Richmond South

2100 W Hundred Rd, Chester, VA

Free Cancellation

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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 Place Richmond/Chester

13148 Kingston Ave, Chester, VA

Free Cancellation

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This hotel features a restaurant, a 24-hour gym, and a bar/lounge. 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 full breakfast and free self parking.

Pool

Breakfast included

SpringHill Suites Chester

12301 REDWATER CREEK ROAD, Chester, VA

Free Cancellation

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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

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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

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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

Virginia Commonwealth University

4.5/5(414 reviews)

Explore the campus of Virginia Commonwealth University during your stay in Richmond. Stroll along the area's riverfront or experience its great live music.

Broad Street

4/5(681 reviews)

During your trip to Richmond, you can find the perfect gifts to bring home at Broad Street. While you're here, you can savor the top-notch restaurants.

University of Richmond

4.5/5(152 reviews)

Take a campus tour or just explore the area of University of Richmond, during your trip to Richmond. Attend a sporting event or simply enjoy the charming coffeehouses while you're in the area.

Frequently asked questions

How much are vacation packages to Chester?

Your travel fantasies can be realized in Chester from just $301. 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.