Chester Vacation Packages 2025 from $354

Chester flight + hotel vacation packages

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

Westgate Historic Williamsburg Resort

Save 100% on your flight

per person

Aug 30 - Sep 2

found 14 hours ago

Roundtrip flight included

Chicago (ORD) 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.

Barsala At Sphere Apartments

Save 100% on your flight

per person

Jul 31 - Aug 7

found 1 day ago

Roundtrip non-stop flight included

Melbourne (MLB) to Richmond (RIC)

This aparthotel includes free WiFi in public areas and a virtual front desk.

Griffin Hotel, an official Colonial Williamsburg Hotel

Colonial Williamsburg

per person

Aug 30 - Sep 2

found 14 hours ago

Roundtrip flight included

Chicago (ORD) 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.

Club Wyndham Governor’s Green

per person

Aug 30 - Sep 2

found 14 hours ago

Roundtrip flight included

Chicago (ORD) 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.

Club Wyndham Kingsgate

per person

Aug 30 - Sep 2

found 14 hours ago

Roundtrip flight included

Chicago (ORD) to Richmond (RIC)

This Colonial resort features 2 outdoor tennis courts, an outdoor pool, and a restaurant. Bring the family and enjoy the mini golf, children's pool, and arcade/game room. Enjoy the indoor pool and perks like free self parking and free WiFi.

Top Chester hotels deals

Country Inn & Suites by Radisson, Chester, VA

2406 W Hundred Rd, Chester, VA

Free Cancellation

Get rates

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

Red Roof Inn Chester

2405 W Hundred Rd, Chester, VA

Free Cancellation

Reserve now, pay when you stay

Get rates

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

SpringHill Suites Chester

12301 REDWATER CREEK ROAD, Chester, VA

Get rates

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

Comfort Inn Chester - Richmond South

2100 W Hundred Rd, Chester, VA

Free Cancellation

Reserve now, pay when you stay

Get rates

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

Get rates

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

Fairfield Inn By Marriott Richmond Chester

12400 Redwater Creek Rd, Chester, VA

Free Cancellation

Reserve now, pay when you stay

Get rates

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

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

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 $354. 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.