Chester Vacation Packages 2026 from $572

Plan, book, travel with confidence
Better together
Save up to $2,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

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.

Sleep Inn & Suites Prince George near Fort Lee

$572

per person

Nov 21 - Nov 24

found 5 hours ago

Roundtrip non-stop flight included

Sioux Falls (FSD) to Richmond (RIC)

8.6/10 Excellent! (473 reviews)

We loved it! Especially we went for our daughter’s graduation. Very friendly and we loved how it smells so good in the hallways. Staffs, very satisfied with the customer service and especially in the mornings with breakfast with the lady working there, thank you for making us feel like Home.

Reviewed on Oct 9, 2026

Home2 Suites By Hilton Richmond Glenside

$664

per person

Nov 13 - Nov 16

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Richmond (RIC)

8.8/10 Excellent! (276 reviews)

Breakfast closes at 9:00 and left a few customers hungry. It would be nice to have a few grab and go options. The need for a parking permit was odd. I had to go back out to the car at check in and put the parking permit in the car to make sure the car wasn't towed. I am not sure why taking license plates for hotel guests wouldn't suffice.

Reviewed on Sep 30, 2026

Linden Row Inn

Downtown Richmond

$663

per person

Nov 21 - Nov 24

found 5 hours ago

Roundtrip non-stop flight included

Sioux Falls (FSD) to Richmond (RIC)

9.2/10 Wonderful! (1,472 reviews)

Beautiful home

Reviewed on Oct 10, 2026

The Boulevard Inn

Fan District

$769

per person

Nov 22 - Nov 24

found 6 hours ago

Roundtrip non-stop flight included

Sioux Falls (FSD) to Richmond (RIC)

9.8/10 Exceptional! (69 reviews)

This inn is perfectly located if you want to drink and dine in Carytown and that would be enough BUT it is also owned and operated by some wonderful folks who work extra hard to make you comfortable, the linens are nice, the bathrobes are fluffy, there’s a wine and cheese hour as well as a fancy coffee maker, and breakfast was lovely. Put all that together and you have and even better Richmond adventure. Loved our stay!

Reviewed on Oct 6, 2026

Cookie B

$781

per person

Nov 21 - Nov 24

found 5 hours ago

Roundtrip non-stop flight included

Sioux Falls (FSD) to Richmond (RIC)

9.6/10 Exceptional! (9 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Chester

View all trips

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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

Richmond: Guided Hike in James River Park

$35

per adult

100% of travellers recommend

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

Oct 29 - Oct 30

Total with taxes and fees

8.8/10 Excellent! (920 reviews)

"Highly recommended. Probably one of the nicest hotels I’ve stayed in."

Reviewed on Oct 4, 2026

Fairfield Inn By Marriott Richmond Chester

12400 Redwater Creek Rd Chester VA

Fully refundableReserve now, pay when you stay

$98 nightly

$114 total

Oct 18 - Oct 19

Total with taxes and fees

Hyatt Select Richmond/Chester

13148 Kingston Ave Chester VA

Fully refundableReserve now, pay when you stay

$94 nightly

$109 total

Oct 18 - Oct 19

Total with taxes and fees

See all 1,034 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

More vacations you might like

Frequently asked questions

What types of vacation packages are available in Chester?

Chester, a central urban destination known for its family-friendly attractions, offers vacation packages tailored to various travel styles:

Budget: Suburban Studios Chester provides value with amenities like a kitchenette, outdoor pool, and pet-friendly options, with travelers often noting its good value.
Family-friendly: Fairfield Inn By Marriott Richmond Chester, rated 7.8 out of 10 by travelers, features family rooms, free breakfast, and is pet-friendly, praised for its big rooms.
Pet-friendly: Hyatt Select Richmond/Chester welcomes pets and offers an outdoor pool and free breakfast, with travelers often praising the great staff.
Breakfast included: Homewood Suites by Hilton Richmond-Chester, rated 8.9 out of 10 by travelers, includes free breakfast, an indoor pool, and kitchens in its rooms, with travelers highlighting the extremely clean rooms.
Parking: Fairfield Inn By Marriott Richmond Chester is a good choice for those traveling by car, offering plenty of parking, with guests appreciating the ample parking.

How can I save money on a Chester vacation package?

When you bundle, you can save up to 30%*. To save money on a Chester package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

How much does a Chester vacation package cost?

A Chester vacation package typically costs around $800 per adult for a weekend trip, which is the most common duration. Prices for lower-priced bookings start from around $550 per adult, while more extensive packages can reach up to $2,000 per adult.*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.

How do I find cheap Chester vacation package deals?

The cheapest Chester vacation package deals can be as low as around $480 per adult for weekend trips. Separately, May typically has the lowest average monthly price, around $1,180 per adult, for a 3-day trip. Bundling flights and hotel together also typically saves money on a weekend trip — most Chester packages include some savings versus booking separately, typically around $20 per adult. Longer, week-long trips can save even more, often around $55 per adult.Browse cheap vacation packages in Chester on Expedia for current deals.*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.

What is the best time to go to Chester?

The peak months for a Chester vacation package are July and March, which see the highest demand from travelers. These periods are popular for exploring the city's attractions and enjoying outdoor activities.For those seeking a more budget-friendly trip, May tends to offer lower package prices. January is typically the quietest month, which can also be a good time to find deals, though fewer travelers visit during this period.

What's included in a Chester vacation package?

A Chester vacation package lets you combine round-trip flights, a hotel stay, and a rental car. Many hotels in Chester offer convenient access to the city's attractions, and a good number provide airport shuttle service to and from Richmond International Airport (RIC). Additionally, many hotels here offer free breakfast, which can be a practical saving during your trip.Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.

What's the best vacation package for Chester?

For families planning a Chester vacation package, a stay at Fairfield Inn By Marriott Richmond Chester is a strong choice. Rated 7.8 out of 10 by travelers, it offers family rooms, free breakfast, and is pet-friendly, with travelers often praising its big rooms.Travelers seeking value can consider a package built around Suburban Studios Chester. This hotel provides practical amenities like a kitchenette and an outdoor pool, and is pet-friendly, with travelers frequently highlighting its good value.For a comfortable stay, Homewood Suites by Hilton Richmond-Chester is rated 8.9 out of 10 by travelers. It features an indoor pool, kitchens in its rooms, and is pet-friendly, with travelers consistently praising the extremely clean rooms and kind staff.

Is Chester better suited for a beach vacation or a cultural trip?

Chester is primarily an urban destination known for its family-friendly attractions and city experiences, where you can find outdoor activities along the James River, about 4 miles from central Chester, or enjoy sports at Iron Bridge Sports Park, about 6 miles away.The area also has historical significance, with sites related to the American Revolution and the Civil War, offering a glimpse into its past. However, the focus for travelers is generally on its urban amenities and family entertainment.

Is Chester a good choice for a family vacation package?

Chester is a strong choice for family vacation packages, with some of the bookings being family trips. You'll find hotels like Fairfield Inn By Marriott Richmond Chester, rated 7.8 out of 10, which offers family rooms and free breakfast to start your day.The area is rich in family-friendly attractions, including Iron Bridge Sports Park, about 6 miles from central Chester, and the popular amusement park Kings Dominion, about 12 miles away. For outdoor adventures, Pocahontas State Park, about 15 miles from central Chester, provides ample space for recreation.

What is the best time to book a Chester vacation package?

Book your Chester vacation package around 1 week before you travel. This gives you time to secure your preferred flights and hotel while rates are still competitive. Most travelers book between 4 days and about 5 weeks out.August, May, and September are the most popular months for Chester packages, so booking earlier is advisable if you're traveling during any of these months.

What are the top things to do in Chester?

A Chester vacation offers a variety of attractions, from outdoor spaces to family entertainment and shopping:Browse and book things to do in Chester on Expedia.

How many days do you need for a Chester vacation?

Most Chester vacation packages typically last around 3 days, with many travelers choosing weekend trips. This duration allows you to explore key attractions like the James River and Iron Bridge Sports Park.Nearly a third of travelers opt for week-long trips, which provide more time to visit destinations such as Kings Dominion, about 12 miles away, or to delve deeper into the area's offerings. A select few also choose extended two-week trips for a more comprehensive experience.

Is Chester a good destination for a weekend vacation?

Chester is an excellent choice for a weekend vacation package, as most travelers specifically choose weekend trips to this destination. In just a few days, you can enjoy outdoor activities along the James River, visit the Iron Bridge Sports Park, or explore shopping at Southpark Mall, about 7 miles from central Chester.While many travelers opt for longer stays to experience more of the area, a focused weekend trip to Chester still offers plenty to see and do.

Do you need to rent a car in Chester, or is public transport enough?

For a Chester vacation package, renting a car is highly recommended for maximum flexibility. Chester is a central urban destination that functions as a bedroom community, with attractions spread out across the area. Having a car allows you to easily reach places like the James River, about 4 miles from central Chester, Iron Bridge Sports Park, about 6 miles away, or Kings Dominion, about 12 miles from the city center.While local taxis and ride-share apps are available, a rental car provides the most convenient way to explore at your own pace. When booking Chester vacation packages with flights, you'll typically arrive at Norfolk International Airport (ORF) or Richmond International Airport (RIC), both of which are best accessed by car.

Are Chester vacation package hotels conveniently located?

Chester vacation package hotels are generally conveniently located within a few miles of central Chester, offering good access to the area. For example, Hampton Inn by Hilton Richmond Chester, rated 9.6 out of 10, is about 2 miles from central Chester.Homewood Suites by Hilton Richmond-Chester, rated 8.9 out of 10, and Courtyard by Marriott Richmond Chester, rated 8.6 out of 10, are both about 3 miles from the city center. Even properties like Candlewood Suites Chester Richmond by IHG, rated 8.7 out of 10, are about 5 miles away, keeping you within easy reach of local attractions.

Are there vacation package hotels in Chester within walking distance of restaurants and shops?

Yes, some Chester vacation package hotels are conveniently located within walking distance of shopping and dining options, particularly those near larger retail centers. For instance, La Quinta Inn & Suites by Wyndham Richmond-Midlothian, rated 7.8 out of 10, and Hampton Inn Richmond-Midlothian Turnpike, rated 7.7 out of 10, are both about a 5-minute walk from Chesterfield Towne Center.Also near the center, the 4-star DoubleTree by Hilton Richmond - Midlothian, rated 7.8 out of 10, is about a 10-minute walk away. These locations provide easy access to a variety of shops and restaurants.

Can I change or cancel my Chester vacation package if my plans change?

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Do One Key members get extra savings when booking Chester vacation packages?

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

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

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Chester vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

How do I find last-minute vacation packages to Chester?

To find last-minute vacation packages to Chester, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

How does free cancellation work on Chester vacation packages?

Free cancellation on a Chester vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Is it cheaper to book a Chester vacation as a package or separately?

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Chester getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Why should I book my Chester vacation package with Expedia?

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

Explore a world of travel with Expedia

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

Chester Vacations from $572

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

Sleep Inn & Suites Prince George near Fort Lee

Home2 Suites By Hilton Richmond Glenside

Linden Row Inn

The Boulevard Inn

Cookie B

Stay near popular Chester attractions

Henricus Historical Park

Parker's Battery Park

Dutch Gap Conservation Area

Presquile National Wildlife Refuge

The Lazy Daisy

Perkinson Center for the Arts Foundation

Cultural Center of India

What to do in Chester

Historic Trolley Tour

The Haunted History of Richmond tour

Richmond: Guided Hike in James River Park

Chester Hotel Deals

SpringHill Suites Chester

Fairfield Inn By Marriott Richmond Chester

Hyatt Select Richmond/Chester

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

Go further with the Expedia app