Chester Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Top hotels in Chester

Hyatt Place Richmond/Chester

Hyatt Place Richmond/Chester

3 out of 5
13148 Kingston Ave, Chester, VA
Fully refundableReserve now, pay when you stay
The price is S$166 per night from 10 Aug to 11 Aug
S$166
10 Aug - 11 Aug
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
"This hotel was in the midst of upgrading it's facility. However, the room was clean and spacious and readily accommodated our stay. We didn't get a chance to take advantage of the breakfast, but the food variety looked appealing."

Reviewed on 29 Jul, 2025

Hyatt Place 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
The price is S$133 per night from 10 Aug to 11 Aug
S$133
10 Aug - 11 Aug
includes taxes & fees
7.4/10 Good! (1,002 reviews)
"Location is great, need to upgrade security and cameras"

Reviewed on 28 Jul, 2025

Country Inn & Suites by Radisson, Chester, VA
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
The price is S$147 per night from 10 Aug to 11 Aug
S$147
10 Aug - 11 Aug
includes taxes & fees
8.2/10 Very Good! (807 reviews)
"During our recent 4-day stay, our room was not cleaned at all, and we had to request fresh towels twice before they were provided. This was disappointing and not the level of service we expected. That said, the room itself was comfortable, and we did enjoy the breakfast each morning."

Reviewed on 29 Jul, 2025

Fairfield Inn By Marriott Richmond Chester
See all 927 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.

Popular places to visit

The National

Get tickets for a show at The National, a popular theatre in Richmond. Amble around this romantic area's riverfront or attend a sporting event.

The National

What to do in Chester

Historic Trolley Tour

Historic Trolley Tour

S$54
per adult
100% of travellers recommend
Historic Trolley Tour
Group Shot at the Virginia State Capitol!

Richmond Landmark Segway Tour

S$70
per adult
Richmond Landmark Segway Tour
See all activities in Chester

Frequently asked questions

How much does a Chester holiday package cost?
You can snap up a holiday package to this popular destination on Expedia. However, how much your holiday 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?
If you're looking to snag a cheap Chester holiday package, consider planning a trip in November, December and January. You're likely to find lower rates on hotels and airfares during these months — perfect for travellers wishing to save money.
How many days is enough for Chester?
With around 2 days, you'll have enough time to experience popular neighbourhoods like Bellwood and Woodvale during your Chester holiday. Be sure to also add Dutch Gap Conservation Area and Henricus Historical Park to your must-do list. Searching for more adventures? Consider venturing outside of Chester on tours and day trips.
Is it worth booking a holiday package to Chester?
It's easy to see why a Chester holiday is on the must-do list of many travellers. Major attractions like Iron Bridge Sports Park are just the beginning 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 holiday as a package?
You can enjoy significant savings on your Chester break by booking a customised holiday 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 holiday 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. Pick your travel dates: The things you plan to do in Chester and your favourite season will help you decide when to travel.
  2. Set your budget: Factor in expenses like flights, transportation and food when working out how much to put aside for your trip to Chester. Then, choose a property that works with your budget, whether that's an economical option or a high-end retreat.
  3. Work out your trip length: Consider how long you want to spend exploring Chester. Plan your days so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Bundle your airfare and accommodation: Once you've settled on your travel dates and duration, lock in the perfect Chester holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.