Chester Vacations from $299

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Your Chester Vacation

Reserve a Chester vacation package that includes everything you need without any unnecessary extras. Great for nightlife, cafes and festivals, consider staying in the neighborhood of Downtown Richmond. A trip to Chester is an ideal opportunity to do a bit of sightseeing. Be sure to visit well-known attractions like Iron Bridge Sports Park, Henricus Historical Park and The Lazy Daisy. A few quick clicks is all it takes to build your dream Chester vacation on Expedia.

The Latest Chester 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
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
8.4/10 Very Good! (1,006 reviews)
I loved everything about it.

Reviewed on Jul 1, 2025

The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Save 100% on your flight
per person
Aug 15 - Aug 22
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
9/10 Wonderful! (1,247 reviews)
The rooms! Hands down the best room I've ever stayed in given the price.

Reviewed on Jun 30, 2025

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
per person
Aug 13 - Aug 17
found 22 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
9.8/10 Exceptional! (283 reviews)
This elegant, historic Inn is perfect. The rooms are large and clean, the staff are friendly and professional, the on-site dining is delicious, and it's within walking distance from historic Colonial Williamsburg and just minutes away from Busch Gardens. We highly recommend!

Reviewed on Jul 1, 2025

Vacation Village At Williamsburg

Vacation Village At Williamsburg

3 out of 5
Save 100% on your flight
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
8.8/10 Excellent! (1,459 reviews)
Old but clean . Great for a family vacation

Reviewed on Jun 30, 2025

Linden Row Inn

Linden Row Inn

3 out of 5
Downtown Richmond
Save 100% on your flight
per person
Aug 15 - Aug 22
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
9.2/10 Wonderful! (1,060 reviews)
Everything related to the hotel was awesome. Very old and charming building, I could stay there for years. No laundry or parking on site though. Only thing that was irritating was panhandling in the area, not that it’s the hotel’s fault.

Reviewed on Jun 25, 2025

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Discover the most popular places to visit in Chester

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
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
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

What to do in Chester

Historic Trolley Tour

Historic Trolley Tour

$42
per adult
Historic Trolley Tour
Richmond: Guided Hike in James River Park

Richmond: Guided Hike in James River Park

$29
per adult
Richmond: Guided Hike in James River Park
Ascending the Capitol Steps

Haunted Capitol Hill Ghost Tour

$27
per adult
100% of travellers recommend
Haunted Capitol Hill Ghost Tour
See all activities in Chester

Chester Hotel Deals

Red Roof Inn Chester
Red Roof Inn Chester
2 out of 5
2405 W Hundred Rd, Chester, VA
Fully refundableReserve now, pay when you stay
$78 nightly
The price is $91 total per night from Jul 7 to Jul 8
$91 total
Jul 7 - Jul 8
Total includes taxes and fees
7/10 Good! (763 reviews)
"Very comfortable beds, large rooms with plenty of space. Wonderful air conditioning that was constant through the night. The shower was good, decent temperature and pressure, and it was accessible."

Reviewed on Jun 28, 2025

Red Roof Inn Chester
Country Inn & Suites by Radisson, Chester, VA
Country Inn & Suites by Radisson, Chester, VA
3 out of 5
2406 W Hundred Rd, Chester, VA
Fully refundable
$88 nightly
The price is $103 total per night from Jul 13 to Jul 14
$103 total
Jul 13 - Jul 14
Total includes taxes and fees
7.2/10 Good! (1,005 reviews)
"Clean, well kept"

Reviewed on Jun 28, 2025

Country Inn & Suites by Radisson, Chester, VA
Comfort Inn Chester - Richmond South
Comfort Inn Chester - Richmond South
2.5 out of 5
2100 W Hundred Rd, Chester, VA
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $94 total per night from Jul 6 to Jul 7
$94 total
Jul 6 - Jul 7
Total includes taxes and fees
7.4/10 Good! (996 reviews)
"Staff was courteous and helpful."

Reviewed on May 18, 2025

Comfort Inn Chester - Richmond South
See all 917 properties in Chester
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.

Find the Best Chester Vacation Packages

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Richmond Intl. Airport (RIC)
Population
21,000
Max Temp Winter
50ºF
Max Temp Summer
90ºF
Top Sights
Iron Bridge Sports Park, Keystone Antique Truck and Tractor Museum and Swift Creek Mill Theatre

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Frequently asked questions

How much does a Chester vacation package cost?
You can snap up a vacation package to this popular destination from $299 on Expedia. However, how much your vacation to Chester costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Chester?
September, November and December are great times to search for cheap Chester vacation packages. Choosing to travel in less busy months means you can usually find lower prices on accommodations and flights.
How many days is enough for Chester?
Allow at least 2 days for your Chester vacation if you're hoping to take in all that makes this destination unique. Wander around popular neighborhoods, including Bellwood and Woodvale. Then tick off top sights like Parker's Battery Park and The Lazy Daisy. With a well-planned itinerary, you'll be kept busy with room for some relaxation too. Want to travel beyond Chester? Consider fitting in an excursion or two.
Is it worth booking a vacation package to Chester?
It's no wonder a Chester vacation is on the to-do list of many travelers. Major attractions like Iron Bridge Sports Park are just the start of things to see and do here.
How to find the best Chester package deals?
Bagging a cheap Chester package deal is a cinch with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Chester package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Chester vacation as a package?
You can enjoy significant savings on your Chester break by booking a customized vacation package. Check the "Package" heading, then select your destination and travel dates to see the best flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Chester?
Enjoy incredible bargains by reserving your flights early with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for an impromptu Chester getaway.
How to plan a trip to Chester?

  1. Choose when to go: Check your schedule and pack your bags. Your favorite season and the type of activities available will also help you decide when to visit Chester.
  2. Set a budget: Factor in expenses such as flights, meals and transportation when calculating how much to put aside for your trip to Chester. Then, select a hotel that matches your budget, whether that's an affordable stay or a high-end getaway.
  3. Organize your Chester escape with our trip planning tool: Look for and book accommodations and things to do all in one place. You can also collaborate with family and friends to plan an unforgettable trip to Chester together.
  4. Set the duration of your trip: Start by making a list of all the activities and sights you'd like to experience in Chester. Then, estimate how long you'll need for each, including any travel time.
  5. Bundle your airfare and accommodations: After you've nailed down your trip dates and duration, lock in the right Chester vacation package for you.
  6. Book experiences or activities in advance: Whether it's a ticket to a big attraction or a day trip, you won't have to worry about missing out on the best Chester has to offer. Find all the fun things to do in Chester with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Chester vacation packages?
Your Chester break is meant to be a relaxing escape from your busy life, not a reason for money-related stress. So to allow you a little more flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.