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.
Club Wyndham Kingsgate

Club Wyndham Kingsgate

3 out of 5
Price was $393, price is now $265 per person
$265
per person
Nov 3 - Nov 6
found 12 hours ago
Roundtrip flight included
Boston (BOS) 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.
Griffin Hotel, an official Colonial Williamsburg Hotel

Griffin Hotel, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
Save 100% on your flight
Price was $429, price is now $290 per person
$290
per person
Nov 3 - Nov 6
found 12 hours ago
Roundtrip 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 Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
Save 100% on your flight
Price was $474, price is now $323 per person
$323
per person
Nov 3 - Nov 6
found 12 hours ago
Roundtrip flight included
Boston (BOS) 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.
The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Save 100% on your flight
Price was $510, price is now $355 per person
$355
per person
Nov 3 - Nov 6
found 12 hours ago
Roundtrip flight included
Boston (BOS) 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.
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
Price was $379, price is now $268 per person
$268
per person
Nov 3 - Nov 6
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Free water park access and an outdoor pool are 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 onsite laundry facilities. Enjoy the gym and free perks like continental breakfast and free self parking.

Top Chester hotels deals

Hyatt Place Richmond/Chester

Hyatt Place Richmond/Chester

3 out of 5
13148 Kingston Ave, Chester, VA
Free Cancellation
Reserve now, pay when you stay
$111 nightly
The price is $129 total per night
$129 total
Aug 27 - Aug 28
Total includes taxes and fees
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

Fairfield Inn By Marriott Richmond Chester

2.5 out of 5
12400 Redwater Creek Rd, Chester, VA
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $114 total per night
$114 total
Aug 24 - Aug 25
Total includes 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
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
$88 nightly
The price is $103 total per night
$103 total
Sep 2 - Sep 3
Total includes 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
Comfort Inn Chester - Richmond South

Comfort Inn Chester - Richmond South

2.5 out of 5
2100 W Hundred Rd, Chester, VA
Free Cancellation
Reserve now, pay when you stay
$84 nightly
The price is $97 total per night
$97 total
Aug 25 - Aug 26
Total includes 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
Red Roof Inn Chester

Red Roof Inn Chester

2 out of 5
2405 W Hundred Rd, Chester, VA
Free Cancellation
Reserve now, pay when you stay
$73 nightly
The price is $85 total per night
$85 total
Aug 24 - Aug 25
Total includes taxes and fees
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
Holiday Inn Express Chester by IHG

Holiday Inn Express Chester by IHG

2.5 out of 5
1911 W Hundred Rd, Chester, VA
Free Cancellation
$111 nightly
The price is $129 total per night
$129 total
Sep 4 - Sep 5
Total includes 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
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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

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.

Virginia Commonwealth University
Game of checkers anyone

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.

University of Richmond
Richmond

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.

Broad Street

Frequently asked questions

How much are vacation packages to Chester?
Your travel fantasies can be realized in Chester from just $265. 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

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