Deals on vacations and trips to Chester

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Chester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Westgate Historic Williamsburg Resort

Westgate Historic Williamsburg Resort

3.5 out of 5
Midtown
Save 100% on your flight
Price was $1,048, price is now $527 per person
$527
per person
Jun 13 - Jun 17
found 1 day ago
Roundtrip flight included
New York (JFK) 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.
The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
Save 100% on your flight
Price was $1,000, price is now $688 per person
$688
per person
Jul 6 - Jul 12
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) 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.
Griffin Hotel, an official Colonial Williamsburg Hotel

Griffin Hotel, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
Price was $808, price is now $559 per person
$559
per person
Jun 13 - Jun 17
found 1 day ago
Roundtrip flight included
New York (JFK) 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.
Wedmore Place

Wedmore Place

3.5 out of 5
Save 100% on your flight
Price was $1,107, price is now $780 per person
$780
per person
Jul 6 - Jul 12
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) 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.
Williamsburg Inn, an official Colonial Williamsburg Hotel

Williamsburg Inn, an official Colonial Williamsburg Hotel

5 out of 5
Colonial Williamsburg
Save 100% on your flight
Price was $2,156, price is now $1,524 per person
$1,524
per person
Jun 13 - Jun 17
found 1 day ago
Roundtrip flight included
New York (JFK) to Richmond (RIC)
A full-service spa, 2 restaurants, and 6 outdoor tennis courts are all featured at this luxury hotel. You'll appreciate the indoor pool, bar/lounge, and concierge services.

Top Chester hotels deals

SpringHill Suites Chester

SpringHill Suites Chester

2.5 out of 5
12301 REDWATER CREEK ROAD Chester VA
Free Cancellation
Reserve now, pay when you stay
$120 nightly
The price is $140 total per night
$140 total
May 21 - May 22
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.
Fairfield Inn By Marriott Richmond Chester

Fairfield Inn By Marriott Richmond Chester

3 out of 5
12400 Redwater Creek Rd Chester VA
Free Cancellation
Reserve now, pay when you stay
$107 nightly
The price is $127 total per night
$127 total
May 10 - May 11
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.
Suburban Studios Chester

Suburban Studios Chester

2 out of 5
2403 W Hundred Rd Chester VA
Free Cancellation
Reserve now, pay when you stay
$67 nightly
The price is $78 total per night
$78 total
May 31 - Jun 1
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
Hyatt Select Richmond/Chester

Hyatt Select Richmond/Chester

3 out of 5
13148 Kingston Ave Chester VA
Free Cancellation
Reserve now, pay when you stay
$118 nightly
The price is $137 total per night
$137 total
May 4 - May 5
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

Country Inn & Suites by Radisson, Chester, VA

3 out of 5
2406 W Hundred Rd Chester VA
Free Cancellation
$98 nightly
The price is $114 total per night
$114 total
May 31 - Jun 1
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.
Comfort Inn Chester - Richmond South

Comfort Inn Chester - Richmond South

2.5 out of 5
2100 W Hundred Rd Chester VA
Free Cancellation
$74 nightly
The price is $86 total per night
$86 total
May 29 - May 30
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
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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

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Short Pump Town Center

4.5/5(472 reviews)

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.

Short Pump Town Center
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Kings Dominion

4.5/5(317 reviews)

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.

Kings Dominion
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Virginia Commonwealth University

4.5/5(421 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.

Virginia Commonwealth University

Frequently asked questions

How much are vacation packages to Chester?
Your travel fantasies can be realized in Chester from just $527. 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.

Photos of local treasures

Browse Chester vacation photos for more inspiration

Aerial photo Chester VA USA
The Queens Park Bridge, a landmark of Chester
Richmond_IronBridgeSportsPark_6193094_01

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