Chester Holidays

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Your Chester Holiday

Say farewell to the worries of planning and hello to a Chester holiday package. With your travel details organised before you go, you can focus on discovering the best of this city, starting with Downtown Richmond, which is good for cafes, nightlife and festivals. Eager to explore? Iron Bridge Sports Park, Castlewood and Henricus Historical Park are three of the top places to visit during a trip to Chester. Don't put off exploring this destination any longer. Your perfect Chester holiday is only a few clicks away with Expedia.

Chester Holiday

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Richmond Intl. Airport (RIC)
Population
21,000
Max Temp Winter
10ºC
Max Temp Summer
32ºC
Top Sights
Keystone Antique Truck and Tractor Museum, Iron Bridge Sports Park and Swift Creek Mill Theatre

Our pick of the best Chester Hotel Deals

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 AU$157 per night from 13 July to 14 July
AU$157
13 July - 14 July
includes taxes & fees
7.2/10 Good! (1,004 reviews)
"Fine"

Reviewed on 16 Jun. 2025

Country Inn & Suites by Radisson, Chester, VA
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 AU$139 per night from 1 July to 2 July
AU$139
1 July - 2 July
includes taxes & fees
7/10 Good! (761 reviews)
"Grateful"

Reviewed on 16 Jun. 2025

Red Roof Inn Chester
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 AU$144 per night from 30 June to 1 July
AU$144
30 June - 1 July
includes taxes & fees
7.4/10 Good! (997 reviews)
"Staff was courteous and helpful."

Reviewed on 18 May 2025

Comfort Inn Chester - Richmond South
See all 918 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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

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.

Discover the most popular places to visit in Chester

Richmond

Broad Street

5/5(1 review)

During your trip to Richmond, you can search for that perfect souvenir at Broad Street. While you're here, you can savour the top-notch restaurants.

Broad Street
Maymont Park featuring heritage architecture and a house

Maymont Park

There’s something for everyone at this estate, with plants, animals and a beautiful house to discover.

Maymont Park
Virginia Museum of Fine Arts featuring art and a city

Virginia Museum of Fine Arts

Home to 22,000 works of art covering 5,000 years of history, this museum has something for everyone.

Virginia Museum of Fine Arts

What to do in Chester

Historic Trolley Tour

Historic Trolley Tour

AU$65
per adult
Historic Trolley Tour
Richmond: Guided Hike in James River Park

Richmond: Guided Hike in James River Park

AU$45
per adult
Richmond: Guided Hike in James River Park
“Our guide was awesome, kind and very knowledgeable about the area and each restaurant. I highly recommend this company and we will be taking the other tours they offer.” - River City Food Tours guest

Arts District Food Tour in Richmond with Discover Richmond

AU$145
per adult
Arts District Food Tour in Richmond with Discover Richmond
See all activities in Chester
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.