Chester Holidays

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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Chester

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
The price is S$116 per night from 7 Jul to 8 Jul
S$116
7 Jul - 8 Jul
includes taxes & fees
7/10 Good! (765 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 28 Jun, 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
The price is S$131 per night from 13 Jul to 14 Jul
S$131
13 Jul - 14 Jul
includes taxes & fees
7.4/10 Good! (1,000 reviews)
"Clean, well kept"

Reviewed on 28 Jun, 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
The price is S$120 per night from 7 Jul to 8 Jul
S$120
7 Jul - 8 Jul
includes taxes & fees
7.4/10 Good! (996 reviews)
"austin from the front desk was amazing. very friendly and accommodating"

Reviewed on 30 Jun, 2025

Comfort Inn Chester - Richmond South
See all 914 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
Historic Trolley Tour
Picture 4 for Activity Richmond Ghosts: Sinister Scares of Shockoe Bottom Tour

Richmond Ghost Tours: Sinister Secrets of Shockoe Bottom

S$35
per adult
80% of travellers recommend
Richmond Ghost Tours: Sinister Secrets of Shockoe Bottom
Richmond: Guided Hike in James River Park

Richmond: Guided Hike in James River Park

S$37
per adult
Richmond: Guided Hike in James River Park
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.