Chester Holidays from £658

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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.

Top Chester Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Howard Johnson by Wyndham Williamsburg

Howard Johnson by Wyndham Williamsburg

2 out of 5
per person
11 Oct - 18 Oct
found 1 day ago
Return direct flight included
London (LON) to Richmond (RIC)
6.4/10 (1,018 reviews)
Easy access to shopping

Reviewed on 31 Jul 2025

King’s Creek Resort by Spinnaker

King’s Creek Resort by Spinnaker

4 out of 5
per person
11 Oct - 18 Oct
found 1 day ago
Return direct flight included
London (LON) to Richmond (RIC)
8.8/10 Excellent! (59 reviews)
Super close to Water Country USA. Ants were a slight problem but that’s the season we are in. Everyone was really nice at the property. Kitchen/living room was very small in the 1 bedroom when the sleeper sofa was pulled out.

Reviewed on 11 Jul 2025

Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
per person
11 Oct - 18 Oct
found 1 day ago
Return direct flight included
London (LON) to Richmond (RIC)
8.8/10 Excellent! (1,001 reviews)
Staff and river pool was excellent! Room was not clean the mirror had a prior message from a guest and there was a used wash cloth in my tub. Found an old package of NyQuil on the floor under the bed. Sheets had old stains. The walkway needed to be swept and there was stuff in the gutters on top of door. The amenities are excellent but the rooms are in desperate need of upkeep and upgrading. The bed felt like sleeping on a brick.

Reviewed on 30 Jul 2025

Days Hotel by Wyndham Williamsburg I-64

Days Hotel by Wyndham Williamsburg I-64

2.5 out of 5
per person
11 Oct - 18 Oct
found 1 day ago
Return direct flight included
London (LON) to Richmond (RIC)
6.2/10 (27 reviews)
Indoor and outdoor pool, great staff and clean,comfy bed, plus breakfast.

Reviewed on 13 Jul 2025

Holiday Inn Express Williamsbrg Busch Gardens Area by IHG

Holiday Inn Express Williamsbrg Busch Gardens Area by IHG

2.5 out of 5
per person
11 Oct - 18 Oct
found 1 day ago
Return direct flight included
London (LON) to Richmond (RIC)
9.2/10 Wonderful! (1,085 reviews)
Very accommodating for everything I needed.

Reviewed on 31 Jul 2025

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

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 £64 per night from 5 Aug to 6 Aug
£64
5 Aug - 6 Aug
includes taxes & fees
7/10 Good! (787 reviews)
"the room a/c was set on 72 the room was at 65 couldn't get it any different brrr"

Reviewed on 20 Jul 2025

Red Roof Inn 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 £97 per night from 24 Aug to 25 Aug
£97
24 Aug - 25 Aug
includes taxes & fees
8.2/10 Very Good! (1,010 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 £78 per night from 10 Aug to 11 Aug
£78
10 Aug - 11 Aug
includes taxes & fees
7.4/10 Good! (1,006 reviews)
"Location is great, need to upgrade security and cameras"

Reviewed on 28 Jul 2025

Country Inn & Suites by Radisson, Chester, VA
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

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

Bring your family to Kings Dominion and enjoy the excitement of this theme park in Doswell. Experience the festivals or attend a sporting event in this family-friendly area.

Kings Dominion

What to do in Chester

Historic Trolley Tour

Historic Trolley Tour

£31
per adult
100% of travellers recommend
Historic Trolley Tour
Group Shot at the Virginia State Capitol!

Richmond Landmark Segway Tour

£41
per adult
Richmond Landmark Segway Tour
See all activities in Chester

Frequently asked questions

How much does a Chester travel package cost?
From as low as £658. 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.

* 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.