Chester Holidays

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Your Chester Holiday

Reserve a Chester holiday package that includes everything you need without any unnecessary extras. Great for nightlife, cafes and festivals, consider staying in the neighbourhood 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 holiday on Expedia.

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

Comfort Inn Chester - Richmond South
Comfort Inn Chester - Richmond South
2.5 out of 5
2100 W Hundred Rd, Chester, VA
Stay at this business-friendly hotel in Chester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms in ...
7.4/10 Good! (997 reviews)
"Staff was courteous and helpful."

Reviewed on 18 May 2025

Comfort Inn Chester - Richmond South
Red Roof Inn Chester
Red Roof Inn Chester
2 out of 5
2405 W Hundred Rd, Chester, VA
Stay at this hotel in Chester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms in their reviews. Popular ...
7/10 Good! (756 reviews)
"The entire staff was truly amazing.."

Reviewed on 8 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
Stay at this 3-star business-friendly hotel in Chester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean ...
7.2/10 Good! (1,000 reviews)
"Room was spacious, clean, comfortable. Bed and pillows super comfy. Hot buffet breakfast had nice options and very tasty: waffles, french toast, sausage, eggs, assorted pastries, fresh fruit, yogurt and cereals. Staff friendly and helpful. Nice pool and exercise room. Non-smoking facility. A few ..."

Reviewed on 6 Jun 2025

Country Inn & Suites by Radisson, Chester, VA
See all 913 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

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Chester travel package cost?
From as low as . Yes, you read that correctly. Our Chester travel packages are the best way to make your budget go further. Combine your favourite hotels, flights and car rentals and get to know this top destination.
If I'm not able to travel, can I cancel my Chester travel package?
Certainly, and we’ll help you every step of the way. You may be able to cancel or change your Chester travel package for free within 24 hours of booking. However, you may incur a fee from your hotel, airline or car rental company if you booked more than 24 hours ago. If your circumstances unexpectedly change, browse our Customer Service Portal for further information.
How do I get a cheap travel package to Chester?
One word: bundle. Flights, hotels and rental cars — combine whatever you need into a Chester travel package and save. Score even more bargains when you include extras such as tours or experiences to your booking. But that’s not the only impressive part. You have the flexibility to customize your holiday your way. We offer over 550 airlines and 1,000,000 properties all over the world, so that everyone has a chance to travel and live out those holiday fantasies.
Does Expedia offer Book Now, Pay Later Chester holidays?
Your bank balance shouldn’t get in the way of escaping on holiday, so Expedia has devised a solution to help. Now that we’ve joined forces with online lender Klarna, it’s easier than ever to book your dream getaway without making a dent in your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your trip. Consider one of these flexible payment options:

  • Pay monthly holidays: Jet off on that dream holiday sooner with Klarna’s manageable monthly instalment plans. If paying bite-sized amounts each month works for you, choose this option at checkout.
  • Pay in instalments holidays: If you’d like to pay for your getaway across multiple transactions, holidays paid in instalments might be the best option for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: When you come across an amazing deal but don’t have the full amount yet, Klarna’s low deposit holiday plan will help you secure your getaway.

Where should I stay in Chester?
Stay where the action happens. Many visitors favor hotels around top attractions, such as Henricus Historical Park, Iron Bridge Sports Park and Presquile National Wildlife Refuge.
What are the top hotels in Chester?
One of the most popular places to stay in Chester is Suburban Extended Stay Hotel Chester I-95, in the neighbourhood of Woodvale. Roam around the city by day and then put your feet up in this home away from home after sunset.
How far in advance should I book my Chester holiday?
While not all air carriers advertise tickets early, you can usually compare international fares on Expedia up to 12 months in advance. This is the time when you’ll bag some fantastic bargains. If you’re booking at the last minute, you could still be in luck. Low prices sometimes become available only weeks before departure.
What does an Expedia Chester travel package include?
Packages include hotels, rental cars and flights, but you can mix and match them to create your dream Chester holiday. You can also add on fun things like experiences and activities once you’ve made your booking. You’re in control! When you bundle your bookings with Expedia, you’ll enjoy discounts you won’t find elsewhere.
What should I know before booking a Chester travel package?
When you book your flights, hotels and car rentals together, you’ll score terrific discounts. Whether you’re planning a beach break in a villa or prefer to stay in a convenient hotel in the city, Expedia will make it happen for less.
Can I choose my airline with a Chester Expedia travel package?
Yes — that’s one of the best things about an Expedia travel package. You can pick and choose your flights, hotels and more. We have more than 550 airline partners worldwide, so you have loads of choice when arranging your Chester escape.

Discover the most popular places to visit in Chester

Maymont Park featuring a house and heritage architecture

Maymont Park

This grand estate is a family favorite with a petting zoo, native wildlife and a preserved 19th-century mansion.

Maymont Park
Lewis Ginter Botanical Garden which includes a park

Lewis Ginter Botanical Garden

Spend some time admiring the beautiful and diverse floral displays featured in this superb botanical garden, one of the finest in the country.

Lewis Ginter Botanical Garden

Kings Dominion

5/5(1 review)

Enjoy the excitement at Kings Dominion and see why this is a favourite theme park in Doswell. Experience the festivals or attend a sporting event in this family-friendly area.

Kings Dominion

Unmissable things to do in Chester

Historic Trolley Tour

Historic Trolley Tour

£31
per adult
Historic Trolley Tour
Richmond: Guided Hike in James River Park

Richmond: Guided Hike in James River Park

£21
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

£69
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. Flight-inclusive packages are ATOL protected.