Chester Vacations

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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.

Discover the most popular places to visit in Chester

Virginia Commonwealth University

Virginia Commonwealth University

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

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

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

What to do in Chester

Historic Trolley Tour

Historic Trolley Tour

$42
per adult
100% of travellers recommend
Historic Trolley Tour
Richmond: Guided Hike in James River Park

Richmond: Guided Hike in James River Park

$35
per adult
Richmond: Guided Hike in James River Park
See all activities in Chester

Chester Hotel Deals

Hyatt Place Richmond/Chester

Hyatt Place Richmond/Chester

3 out of 5
13148 Kingston Ave, Chester, VA
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $129 total per night from Sep 25 to Sep 26
$129 total
Sep 25 - Sep 26
Total with taxes and fees
8.2/10 Very Good! (1,006 reviews)
Peaceful Vacation!!!
"Everything was clean nice and quiet and comfortable!!!"

Reviewed on Sep 14, 2025

Hyatt Place Richmond/Chester
Fairfield Inn By Marriott Richmond Chester

Fairfield Inn By Marriott Richmond Chester

2.5 out of 5
12400 Redwater Creek Rd, Chester, VA
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $117 total per night from Sep 28 to Sep 29
$117 total
Sep 28 - Sep 29
Total with taxes and fees
8.2/10 Very Good! (832 reviews)
"Nice restaurants near nearby in walking distance alot of stores in walking distance. Very nice and friendly staff."

Reviewed on Sep 2, 2025

Fairfield Inn By Marriott Richmond 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
$89 nightly
The price is $103 total per night from Oct 20 to Oct 21
$103 total
Oct 20 - Oct 21
Total with taxes and fees
7.4/10 Good! (1,003 reviews)
Great hotell clean rooms convenient location
"Clean comfy room some minor damages in the bathroom and stains on carpet and walls but looked to be old. Great bed and large screen tv w lots of channels. Everything was clean and kitchen items all worked. Coffee also available in the room. Hot and cold Breakfast was good and located across from ..."

Reviewed on Sep 9, 2025

Country Inn & Suites by Radisson, Chester, VA
See all 911 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.

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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 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.