Chester Vacation Packages 2026 from $474

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Your Chester Vacation

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

The Latest Chester vacation packages

Price found within the past 48 hours. Click for updated prices.

Westgate Historic Williamsburg Resort

Midtown

Save 100% on your flight

$474

per person

Oct 6 - Oct 10

found 1 day ago

Roundtrip flight included

New York (NYC) to Richmond (RIC)

8.6/10 Excellent! (1,000 reviews)

Lovely spot that was very close to where I needed to be so could walk. Rooms were clean with a full kitchen. Comfortable beds, nice A/C, great fitness room. It's more of a "motel" so people are walking by your room so curtains can't be opened unless you want everybody to see in.

Reviewed on Aug 23, 2026

Griffin Hotel, an official Colonial Williamsburg Hotel

Colonial Williamsburg

$632

per person

Oct 11 - Oct 14

found 1 day ago

Roundtrip flight included

New York (NYC) to Richmond (RIC)

8.8/10 Excellent! (859 reviews)

Very spacious quiet clean rooms

Reviewed on Aug 24, 2026

The Commonwealth

Downtown Richmond

Save 100% on your flight

$888

per person

Nov 11 - Nov 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Richmond (RIC)

8.8/10 Excellent! (1,386 reviews)

Wedmore Place

Save 100% on your flight

$512

per person

Oct 15 - Oct 18

found 1 day ago

Roundtrip flight included

Islip (ISP) to Richmond (RIC)

9.4/10 Exceptional! (1,001 reviews)

Wedmore Place was an awesome place to stay. It gave you the sense of staying in a historic castle or inn. The grounds were lovely and felt removed and quiet. There was a great sense of peace here. Walking distance from the winery for a tasting and a tavern for a great elevated dining experience. Overall a great place. For people who like very hot showers or strong water pressure, my room did not have that. It wasn't bad for me but I know people like it more intense than me. Also, the thermostat was just kind of odd/confusing, but once we figured it out we were comfortable. Oh, and if you need air movement/noise, bring a fan. The bed was awesome. The atmosphere of the building was awesome. The breakfast was awesome. I would definitely stay here again.

Reviewed on Aug 23, 2026

Kingsmill Resort

Kingsmill

$755

per person

Oct 18 - Oct 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Richmond (RIC)

8.8/10 Excellent! (1,011 reviews)

This place is super gorgeous and fun, but it does need some upgrades. The condo we stayed in was very small (double beds) and we could hear both the dog and the conversation in the next room over. It didn't really feel private, and the dog was super annoying because it barked or whined extensively during the day and at night. I called/texted the concierge, but they wanted me to figure out which room it was instead of looking on their own map. I complied, but it wasn't easy for me to figure out which condo it was because the layout was odd. The concierge was polite, but he didn't seem to care that this was affecting our stay. (If a Pro Golfer were staying there and complained about noise, I'm pretty sure they wouldn't ask them to check the property and figure it out.) Things like ice and beverages weren't easily accessible due to the condo layout. The lobby was beautiful, but the shop inside was closed by 9pm. The rooms need new carpet and upgrading and the mattresses felt cheap. The pools and gym were all amazing.

Reviewed on Aug 25, 2026

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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.

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The Lazy Daisy

7.4/10 (39 reviews)

This charming boutique showcases upcycled furniture and handmade gifts from local artisans in a cozy setting. Browse one-of-a-kind treasures while engaging with staff about each piece's craftsmanship.

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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.

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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.

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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.

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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 savor the top-notch restaurants.

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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 savor the top-notch restaurants.

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What to do in Chester

Historic Trolley Tour

$45

per adult

100% of travellers recommend

Down in the Shokoe Bottom, the most haunted neighborhood with 350+ years of history and hauntings!

The Haunted History of Richmond tour

$30

per adult

See all activities in Chester

Chester Hotel Deals

SpringHill Suites Chester

12301 REDWATER CREEK ROAD Chester VA

Fully refundableReserve now, pay when you stay

$120 nightly

$140 total

Sep 17 - Sep 18

Total with taxes and fees

Fairfield Inn By Marriott Richmond Chester

12400 Redwater Creek Rd Chester VA

Fully refundableReserve now, pay when you stay

$98 nightly

$114 total

Aug 30 - Aug 31

Total with taxes and fees

Quality Inn Chester - South Richmond

12711 Old Stage Rd Chester VA

Fully refundable

$77 nightly

$89 total

Aug 29 - Aug 30

Total with taxes and fees

See all 1,036 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.

Find the Best Chester Vacation Packages

Things to do in and around Chester

Chester, Virginia, offers a delightful mix of activities perfect for families and business travelers alike. Explore the local shopping mall and adventure arcade for fun experiences. Enjoy outdoor adventures and exciting tours that highlight the area's natural beauty. With a focus on sightseeing and engaging local activities, Chester is a great destination for those looking to relax and have fun in a vibrant community atmosphere.

Shopping

In Chester, you can shop at The Lazy Daisy for unique gifts and MastRpieces Unlimited, both located in the area. If you're up for a drive, visit Southpark Mall, 8 miles away, offering a variety of stores and entertainment options for a vibrant shopping experience.

Recreation

Parker's Battery Park offers a tranquil atmosphere perfect for relaxation and wellness activities amidst nature. Just 12 miles away, River City Sportsplex provides a variety of recreational options, encouraging an active lifestyle. For cultural enrichment, the Beacon Theatre, located 9 miles away, presents engaging performances and entertainment for all ages.

Adventure

At Iron Bridge Sports Park in Chester, dive into an arcadeAdventureZone filled with excitement for the whole family. Swaders Sports Park, located 8 miles away, offers thrilling activities for adventure seekers. Uptown Alley, 11 miles from Chester, combines arcade fun with family-friendly vibes for an unforgettable experience.

Nightlife

If you're in Chester, don't miss Hanover Tavern, a charming drinking pub located 28 miles away. It offers a lively atmosphere perfect for enjoying drinks and live entertainment, all while soaking up romantic vibes that make for an unforgettable night out.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Chester

Chester, Virginia, is perfect for family, business, or city-themed vacations, offering a blend of historic sites, urban parks, and renowned colleges. Visitors can immerse themselves in the local culture while enjoying outdoor activities and family-friendly experiences. Don't miss the chance to explore Chester's rich history and vibrant community, making it a delightful destination for all types of travelers.

Virginia State University: Located 8 miles from Chester, Virginia State University is a historic college that embodies rich cultural vibes. It offers a unique glimpse into African American history and educational excellence, with beautiful campus architecture and engaging art installations.
Pocahontas State Park: Just 7 miles away, Pocahontas State Park is a national park that invites adventure enthusiasts. With scenic trails, fishing spots, and picnic areas, it's perfect for outdoor activities amidst breathtaking natural beauty.
Castlewood: Situated 3 miles from Chester, Castlewood is a historic house that showcases cultural heritage. Visitors can explore its fascinating architecture and learn about the local history, making it a must-see for history buffs.

Best time to go to Chester

The best time to visit Chester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Chester falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Chester falls in January, visitor numbers are slightly low and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	38.3°F (3.5°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
February	41.9°F (5.5°C)	Light Rain	Mostly Sunny	Average	Slightly Low
March	48.6°F (9.2°C)	Light Rain	Mostly Sunny	Average	Slightly High
April	58.6°F (14.8°C)	Light Rain	Mostly Sunny	Slightly High	Average
May	67.3°F (19.6°C)	Light Rain	Mostly Sunny	Average	Slightly High
June	75.6°F (24.2°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
July	80.1°F (26.7°C)	Light Rain	Mostly Sunny	Slightly High	Average
August	77.9°F (25.5°C)	Light Rain	Mostly Sunny	Average	Average
September	72.1°F (22.3°C)	Light Rain	Mostly Sunny	Average	Average
October	61.5°F (16.4°C)	Light Rain	Mostly Sunny	Average	Average
November	49.8°F (9.9°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	43.3°F (6.3°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low

Tips to save on your trip to Chester

Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
Consider traveling to Chester during the low season (December to February) for more affordable options.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Chester Essential Information

Language	English
Currency	U.S dollars
Closest Airport	Richmond Intl. Airport (RIC)
Population	21,000
Max Temp Winter	50ºF
Max Temp Summer	90ºF
Top Sights	Iron Bridge Sports Park, Keystone Antique Truck and Tractor Museum and Swift Creek Mill Theatre

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Frequently asked questions

How much does a Chester vacation package cost?

You can snap up a vacation package to this popular destination from $474 on Expedia. However, how much your vacation 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?

September, November and December are great times to search for cheap Chester vacation packages. Choosing to travel in less busy months means you can usually find lower prices on accommodations and flights.

How many days is enough for Chester?

Allow at least 2 days for your Chester vacation if you're hoping to take in all that makes this destination unique. Wander around popular neighborhoods, including Bellwood and Woodvale. Then tick off top sights like Parker's Battery Park and The Lazy Daisy. With a well-planned itinerary, you'll be kept busy with room for some relaxation too. Want to travel beyond Chester? Consider fitting in an excursion or two.

Is it worth booking a vacation package to Chester?

It's no wonder a Chester vacation is on the to-do list of many travelers. Major attractions like Iron Bridge Sports Park are just the start 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 vacation as a package?

You can enjoy significant savings on your Chester break by booking a customized vacation 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 vacation 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?

Choose when to go: Check your schedule and pack your bags. Your favorite season and the type of activities available will also help you decide when to visit Chester.
Set a budget: Factor in expenses such as flights, meals and transportation when calculating how much to put aside for your trip to Chester. Then, select a hotel that matches your budget, whether that's an affordable stay or a high-end getaway.
Organize your Chester escape with our trip planning tool: Look for and book accommodations and things to do all in one place. You can also collaborate with family and friends to plan an unforgettable trip to Chester together.
Set the duration of your trip: Start by making a list of all the activities and sights you'd like to experience in Chester. Then, estimate how long you'll need for each, including any travel time.
Bundle your airfare and accommodations: After you've nailed down your trip dates and duration, lock in the right Chester vacation package for you.
Book experiences or activities in advance: Whether it's a ticket to a big attraction or a day trip, you won't have to worry about missing out on the best Chester has to offer. Find all the fun things to do in Chester with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Chester vacation packages?

Your Chester break is meant to be a relaxing escape from your busy life, not a reason for money-related stress. So to allow you a little more flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

Chester Vacations from $474

Book a Hotel + Flight or Car together to unlock savings

Room 1

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Chester Vacation

The Latest Chester vacation packages

Westgate Historic Williamsburg Resort

Griffin Hotel, an official Colonial Williamsburg Hotel

The Commonwealth

Wedmore Place

Kingsmill Resort

Stay near popular Chester attractions

Henricus Historical Park

The Lazy Daisy

Dutch Gap Conservation Area

Presquile National Wildlife Refuge

Parker's Battery Park

Cultural Center of India

Perkinson Center for the Arts Foundation

What to do in Chester

Historic Trolley Tour

The Haunted History of Richmond tour

Chester Hotel Deals

SpringHill Suites Chester

Fairfield Inn By Marriott Richmond Chester

Quality Inn Chester - South Richmond

Find the Best Chester Vacation Packages

Things to do in and around Chester

Find the best attractions near Chester

Best time to go to Chester

Tips to save on your trip to Chester

Chester Essential Information

More vacations you might like

Frequently asked questions

Explore a world of travel with Expedia

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