Chester Holidays
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Top hotels in Chester
SpringHill Suites Chester
12301 REDWATER CREEK ROAD Chester VA
Fully refundableReserve now, pay when you stay
S$177
17 Sept - 18 Sept
includes taxes & fees
Fairfield Inn By Marriott Richmond Chester
12400 Redwater Creek Rd Chester VA
Fully refundableReserve now, pay when you stay
S$145
30 Aug - 31 Aug
includes taxes & fees
8.2/10 Very good! (1,010 reviews)
"The room that I stayed in was pretty large had enough space for my family of 4. What we enjoyed the most were the mattress es. The hotel itself was very clean and well maintained. The hotel was mostly booked every night we stayed and the noise lever was very minimal. I would definitely recommend ..."
Reviewed on 23 Aug, 2026
Quality Inn Chester - South Richmond
12711 Old Stage Rd Chester VA
Fully refundable
S$111
26 Aug - 27 Aug
includes taxes & fees
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.
Stay near popular Chester attractions
Henricus Historical Park
8.0/10 (63 reviews)
Step back in time at Henricus Historical Park, a living recreation of America's second English settlement from 1611. Costumed interpreters demonstrate colonial crafts while you explore reconstructed buildings.
Dutch Gap Conservation Area
7.8/10 (52 reviews)
This riverside sanctuary offers diverse ecosystems where bald eagles and ospreys soar above tidal wetlands. Explore the 4.5-mile lagoon loop trail for prime wildlife viewing and James River vistas.
Presquile National Wildlife Refuge
7.2/10 (36 reviews)
This secluded island refuge in the James River serves as a critical sanctuary for migratory birds. Explore three miles of trails through pristine marshes and woodlands with advance permits and your own watercraft.
Parker's Battery Park
7.4/10 (38 reviews)
Explore the original earthworks and artillery positions of this Civil War defensive site along the Howlett Line. The quarter-mile trail offers a peaceful journey through history with informative interpretive displays.
The Lazy Daisy
7.4/10 (39 reviews)
This charming boutique showcases upcycled furniture and handmade gifts from local artisans in a cosy setting. Browse one-of-a-kind treasures while engaging with staff about each piece's craftsmanship.
Cultural Center of India
Enjoy an outing to Cultural Center of India during your stay in Chester. While in this family-friendly area, you can savour the top-notch restaurants.
Perkinson Center for the Arts Foundation
Enjoy an outing to Perkinson Center for the Arts Foundation during your stay in Chester. While in this family-friendly area, you can savour the top-notch restaurants.
What to do in Chester
Downtown Richmond Must-See Landmarks with Self-Guided Audio Tour
S$13
per traveller
80% of travellers recommend
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?
- Pick your travel dates: The things you plan to do in Chester and your favourite season will help you decide when to travel.
- 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.
- 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.
- 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.
