Chesapeake Vacation Packages 2026 from $174

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 Chesapeake Vacation

Lock in a Chesapeake vacation package and concentrate on what matters — enjoying yourself. No more planning headaches, just a lot more free time to uncover what's special about this lively city, such as its rich history and family-friendly attractions. Make your trip to Chesapeake even more fun by including some sightseeing. Greenbrier Mall, Oak Grove Lake Park and Chesapeake City Park are among the popular attractions you'll want to explore. Your perfect Chesapeake vacation is just clicks away. Search flights, hotels and more on Expedia for a trip that's tailored just for you.

The Latest Chesapeake vacation packages

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

Budget Inn Norfolk Va

Willoughby Spit

$174

per person

Dec 12 - Dec 16

found 20 hours ago

Roundtrip flight included

Atlanta (ATL) to Norfolk (ORF)

6/10 (673 reviews)

good

Reviewed on Oct 6, 2026

John Yancey Oceanfront Inn

$469

per person

Nov 9 - Nov 13

found 8 hours ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Norfolk (ORF)

9.2/10 Wonderful! (1,946 reviews)

Great location, good continental breakfast, clean, better than I expected considering how affordable it was.

Reviewed on Oct 4, 2026

Boardwalk Resort and Villas

Northeast Virginia Beach

$469

per person

Nov 13 - Nov 18

found 22 hours ago

Roundtrip flight included

Boston (BOS) to Norfolk (ORF)

8.8/10 Excellent! (1,006 reviews)

Sea Scape Beach and Golf Villas

Sea Scape

$532

per person

Nov 9 - Nov 13

found 8 hours ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Norfolk (ORF)

9.4/10 Exceptional! (182 reviews)

The Barclay Towers Resort Hotel

Northeast Virginia Beach

$457

per person

Dec 11 - Dec 14

found 7 hours ago

Roundtrip flight included

Dallas (DFW) to Norfolk (ORF)

7.8/10 Good! (1,015 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Chesapeake

View all trips

Where to stay in Chesapeake

Find the best Chesapeake areas and neighborhoods for the activities you enjoy most. Learn more about Chesapeake

A wooden pier extending into a calm lake, surrounded by dense trees.

Greenbrier

4 out of top 10 points of interest in this area

If you're spending some time in Greenbrier, Greenbrier Mall and Chesapeake Arboretum are top sights worth seeing.

Deep Creek South

1 out of top 10 points of interest in this area

Suburban community with a rural touch, Deep Creek is connected to the historic Dismal Swamp Canal, a National Historic Civil Engineering Landmark. Located along the original U.S. Highway 17 route, it offers easy access to nearby attractions.

A sunset over a calm river with industrial structures and a large bridge.

Greenbrier East

While visiting Greenbrier East, you might make a stop by sights like Greenbrier Mall and Virginia Beach.

A person standing on a boat deck facing a foggy landscape with a ship in the distance and the sun setting on the horizon.

Greenbrier West

If you're spending some time in Greenbrier West, Bowlero Chesapeake and Rivercrest Play Area are top sights worth seeing.

A coastal cityscape with a large ship docked at a port, modern buildings, and a river.

South Norfolk

South Norfolk might not have many top sights, but Chesapeake Conference Center and Greenbrier Mall are two attractions nearby that you can check out.

Stay near popular Chesapeake attractions

A large building with a prominent arched entrance and a green roof.

Greenbrier Mall

8.4/10 (837 reviews)

This regional shopping center features over 100 stores and eateries, plus a Cinema Café for dining during movies. Families enjoy the supervised soft play area and convenient amenities while shopping.

See properties

A building with a clock tower, surrounded by pink flowers and greenery.

Chesapeake Square Mall

8.2/10 (429 reviews)

Chesapeake Square Mall blends shopping with entertainment at its 12-screen Cinemark XD theater. Visit weekday mornings for a relaxed experience at this regional retail center undergoing a $30 million revitalization.

See properties

Chesapeake Conference Center

7.8/10 (169 reviews)

This versatile 39,000-square-foot venue hosts elegant weddings to professional conferences in Chesapeake, Virginia. The on-site catering team delivers customized dining experiences with free Wi-Fi and parking.

See properties

A wooden bridge over a calm river surrounded by dense forest.

Chesapeake City Park

8.2/10 (180 reviews)

This sprawling 90-acre recreational haven hosts Chesapeake's signature events like the Jubilee and Symphony Under the Stars. Families enjoy the Fun Forest Playground and peaceful walking trails.

See properties

A solitary tree in a swampy area with water around its base.

Lake Drummond

7.8/10 (12 reviews)

Lake Drummond, one of only two natural freshwater lakes in Virginia, sits at the heart of Great Dismal Swamp. Paddle through tea-colored waters while spotting black bears and rare birds in this serene ecosystem.

See properties

Oak Grove Lake Park

7.6/10 (39 reviews)

Encircling a serene 65-acre lake, this park's 1.5-mile trail offers picturesque views and abundant wildlife. Enjoy fishing from accessible platforms or relax at shaded picnic areas overlooking the water.

See properties

Camelot Park

Camelot Park is just one of the places to see in Chesapeake, so why not enjoy the other things to explore during your travels? Stroll along the beautiful beaches or visit the shops in this family-friendly area.

See properties

Chesapeake Veterans' Memorial

8.0/10 (79 reviews)

Learn about the local history of Chesapeake with a stop at Chesapeake Veterans' Memorial. Stroll along the area's beautiful beaches or experience its great live music.

See properties

What to do in Chesapeake

Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin

$43

per adult

80% of travellers recommend

View of the water and the Spirit of Norfolk Dinner Cruise ship

City Cruises Norfolk: Signature Dinner Cruise

$93

per adult

76% of travellers recommend

Buried Beneath the Boardwalk: Neptune Ghouls and Ghost Tours

$24

per adult

See all activities in Chesapeake

Chesapeake Hotel Deals

Comfort Suites Chesapeake - Norfolk

1550 Crossways Blvd Chesapeake VA

Fully refundable

$84 nightly

$99 total

Nov 5 - Nov 6

Total with taxes and fees

YourSpace Hotels Chesapeake

2137 Starmount Parkway Chesapeake VA

Fully refundableReserve now, pay when you stay

$91 nightly

$106 total

Oct 19 - Oct 20

Total with taxes and fees

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

1101 Atlantic Ave Virginia Beach VA

Fully refundable

$76 nightly

$89 total

Oct 28 - Oct 29

Total with taxes and fees

8.2/10 Very Good! (1,603 reviews)

"Great location and friendly staff. However, I’ve never seen cockroaches like I saw in this hotel and the bar below it."

Reviewed on Oct 6, 2026

See all 3,500 properties in Chesapeake

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 Chesapeake Vacation Packages

Things to do in and around Chesapeake

Chesapeake, Virginia, offers a delightful mix of activities for families, couples, and outdoor enthusiasts. Enjoy leisurely strolls along the scenic boardwalk, explore vibrant shopping centers, and indulge in nature walks. Discover friendly attractions, relax at picturesque gazebos, and take in beautiful sightseeing experiences that showcase the area's charm. Whether you're looking for adventure or relaxation, Chesapeake has something for everyone to enjoy.

Shopping

In Chesapeake, you can enjoy shopping at Greenbrier Mall, which offers a variety of stores and entertainment. Chesapeake Square Mall features a similar vibe, perfect for family outings. If you're up for a drive, check out Cedar Lakes Retail Center for more shopping options in a lively atmosphere.

Recreation

Experience the vibrant atmosphere at Harbor Park, where you can catch an exciting game and soak in the energizing sports vibes. For a night of live music, head to The NorVa, a fantastic venue filled with entertainment energy. Enjoy relaxation and nature at Oak Grove Lake Park, perfect for unwinding.

Adventure

Experience the thrill of arcade games at Jillian's Billiards in Chesapeake, where family fun meets adventure. Enjoy outdoor activities and camping at Northwest River Park and Campground, perfect for nature lovers. For tennis enthusiasts, Folkes - Stevens Indoor Tennis Center offers exciting adventure activities a short drive away.

Nightlife

Chesapeake's nightlife features lively spots like Greenbrier Mall’s bars, the trendy downtown scene, and local breweries. Enjoy live music at venues like The Norva in nearby Norfolk or dance at clubs around the area, creating an energetic atmosphere for a memorable night out.

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

Find the best attractions near Chesapeake

Chesapeake, Virginia, is an ideal destination for family, outdoor, and romantic vacations. Visitors can explore a variety of attractions including urban parks, a maritime museum, and a historic college university. The area offers rich cultural experiences and beautiful outdoor settings, particularly around the stunning Chesapeake Bay, making it perfect for travelers seeking both adventure and relaxation.

Norfolk State University: A historic institution deeply rooted in culture, Norfolk State University offers visitors a glimpse into its rich heritage and vibrant student life. The campus features beautiful architecture and engaging events that celebrate diversity and academic excellence.
Norfolk Scope: This lively arena serves as a hub for family-friendly entertainment, hosting concerts, sports events, and community gatherings. Its energetic atmosphere and diverse programming make it a perfect spot for a fun outing with family and friends.
Regent University: A modern campus that embodies a city vibe, Regent University blends academic rigor with a welcoming community. Visitors can explore its stunning facilities and enjoy the tranquil surroundings, making it a great place for reflection and inspiration.

Best time to go to Chesapeake

The best time to visit Chesapeake is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	41.0°F (5.0°C)	Light Rain	Mostly Sunny	Average	Slightly Low
February	43.7°F (6.5°C)	Light Rain	Mostly Sunny	Average	Slightly Low
March	49.3°F (9.6°C)	Light Rain	Mostly Sunny	Average	Average
April	58.6°F (14.8°C)	Light Rain	Mostly Sunny	Slightly High	Average
May	67.1°F (19.5°C)	Light Rain	Mostly Sunny	Average	Average
June	75.2°F (24.0°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
July	79.7°F (26.5°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	78.4°F (25.8°C)	Light Rain	Mostly Sunny	Average	Slightly High
September	73.6°F (23.1°C)	Light Rain	Mostly Sunny	Average	Average
October	64.0°F (17.8°C)	Light Rain	Mostly Sunny	Slightly Low	Average
November	52.9°F (11.6°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	46.4°F (8.0°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low

Tips to save on your trip to Chesapeake

Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Chesapeake.
Consider traveling to Chesapeake 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.

Chesapeake Essential Information

Language	English
Currency	U.S dollars
Closest Airport	Norfolk Intl. Airport (ORF)
Population	235,400
Max Temp Winter	50ºF
Max Temp Summer	85ºF
Top Sights	Portlock Galleries at SoNo, Jillians Billiards and Chesapeake City Park

More vacations you might like

Frequently asked questions

What types of vacation packages are available in Chesapeake?

Chesapeake, known for its family-friendly attractions, offers vacation packages tailored to various travel styles:

Family-friendly: A package with a stay at Residence Inn by Marriott Chesapeake Greenbrier, rated 8.5 out of 10 by travelers, is a great choice, offering family rooms, a game room, and an indoor pool — travelers often praise the super helpful staff and great breakfast.
Romantic: Consider a package featuring Courtyard by Marriott Chesapeake, which includes a bar/lounge and kitchenette, with travelers noting the nice staff and all new rooms.
Best value: For budget-conscious travelers, Candlewood Suites Chesapeake/Suffolk by IHG, rated 7.9 out of 10 by travelers, provides kitchens and is pet-friendly, with guests highlighting the welcoming staff and comfortable rooms.
Pet-friendly: A package with a stay at Hyatt Place Chesapeake, rated 7.7 out of 10 by travelers, welcomes pets and features an indoor pool, with guests often praising its amazing location and staff.
Breakfast included: Fairfield Inn and Suites By Marriott Chesapeake, rated 8.9 out of 10 by travelers, offers free breakfast and an outdoor pool, and travelers frequently mention the good breakfast and super helpful staff.

How can I save money on a Chesapeake vacation package?

When you bundle, you can save up to 30%*. To save money on a Chesapeake 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 Chesapeake vacation package cost?

A Chesapeake vacation package typically costs around $800 per adult for a weekend trip. Lower-priced bookings start from around $450 per adult, while higher-end packages can reach up to $1,550.*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 Chesapeake vacation package deals?

The cheapest Chesapeake vacation package deals can be as low as around $450 per adult for weekend trips. Separately, January typically has the lowest average monthly prices, around $670 per adult, for a 3-day trip, with November following at around $800 per adult for a 3-day trip. Bundling flights and hotel together also helps save money — most Chesapeake vacation package deals include some savings versus booking separately, typically around $45 per adult. Browse cheap vacation packages in Chesapeake 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 Chesapeake?

The best time to go for a Chesapeake vacation package is during the peak booking months of April, May, and June. These months typically see the most travelers enjoying the city's attractions and outdoor activities.For those seeking a more budget-friendly Chesapeake vacation, January and November tend to offer lower package prices, making them good options for value-conscious travelers.

What's included in a Chesapeake vacation package?

A Chesapeake vacation package lets you combine round-trip flights, hotel stays, and rental cars. Many hotels in Chesapeake offer free breakfast, and some also provide airport shuttle services to and from Norfolk International Airport (ORF).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 Chesapeake?

For families visiting Chesapeake, a package with a stay at Residence Inn by Marriott Chesapeake Greenbrier, rated 8.5 out of 10 by travelers, is a strong choice. This hotel, costing around $210 per night, offers family rooms, a game room, an indoor pool, and kitchens, with travelers often praising the super helpful staff, great breakfast, and good food.Couples looking for a romantic getaway might consider a package featuring Courtyard by Marriott Chesapeake. This hotel, around $170 per night, includes a bar/lounge, kitchenette, and restaurant, with travelers noting the nice staff and all new rooms.For the best value, a Chesapeake vacation package built around Candlewood Suites Chesapeake/Suffolk by IHG, rated 7.9 out of 10 by travelers, is ideal. At around $130 per night, it provides kitchens and is pet-friendly, with guests highlighting the welcoming staff and comfortable rooms.*Package availability and prices may change depending on dates and demand.

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

Chesapeake is a central urban destination known for its family-friendly attractions and city amenities. While it offers access to beaches like Ocean View Beach about 6 miles away, a Chesapeake vacation also provides urban experiences and historical sites.Travelers can explore shopping at Greenbrier Mall or enjoy entertainment at the Waterside District, about 2 miles from central Chesapeake. For history enthusiasts, the Battle of Great Bridge site offers a glimpse into the American Revolutionary War.This blend means a Chesapeake vacation can be tailored to include both city exploration and coastal relaxation. Choose a package hotel in central Chesapeake if these attractions are priorities.

Is Chesapeake a good choice for a family vacation package?

Chesapeake is a strong choice for family vacation packages, with some bookings being family trips. Many hotels in Chesapeake feature amenities like family rooms, indoor pools, and game rooms, catering to the needs of traveling families.For instance, Residence Inn by Marriott Chesapeake Greenbrier, rated 8.5 out of 10 by travelers, is a family hotel that includes a kitchen and hot tub, and is about a 15-minute walk from Greenbrier Mall. Travelers frequently praise its top-notch overall experience.Families can also enjoy a day at Ocean View Beach, about 6 miles from central Chesapeake, or explore shopping and entertainment at the Waterside District, about 2 miles away. Your Chesapeake vacation package can be customized to include these family-friendly activities.

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

Book your Chesapeake vacation package around 2 weeks before you travel. This gives you time to secure your preferred flights and hotel while rates are still competitive. Most travelers book between 1 and 5 weeks out.April, May, and June are the most popular months for Chesapeake packages, so booking earlier is advisable if you're traveling during these times.

What are the top things to do in Chesapeake?

A Chesapeake vacation offers a variety of attractions, from shopping and entertainment to historical sites and beaches:Browse and book things to do in Chesapeake on Expedia.

How many days do you need for a Chesapeake vacation?

Most Chesapeake vacation packages last around 3 days, with many travelers opting for weekend trips. This duration allows visitors to explore key attractions like Greenbrier Mall and the Waterside District, or enjoy a day at Ocean View Beach.Nearly a third of travelers choose week-long trips, which provide more time to delve into the city's offerings and perhaps visit additional sites like the Chesapeake Square Mall. A select few travelers also opt for extended stays of around two weeks. Your Chesapeake vacation package can be customized around these activities.

Is Chesapeake a good destination for a weekend vacation?

Chesapeake is a good destination for a weekend vacation package, with most travelers choosing weekend trips. In 1 to 3 days, visitors can comfortably explore popular spots like the Waterside District for entertainment and dining, or enjoy shopping at Greenbrier Mall.A weekend Chesapeake vacation also allows time for a relaxing visit to Ocean View Beach, about 6 miles from central Chesapeake, making it easy to combine urban attractions with coastal relaxation. Your Chesapeake vacation package can be tailored to fit a quick weekend getaway.

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

For Chesapeake vacation packages with flights, a rental car is generally recommended for getting around. While Hampton Roads Transit services some areas, the city's attractions and various neighborhoods are spread out, making a car the most flexible option for exploring.Chesapeake has a network of major roads, including the Hampton Roads beltway (I-64, I-664, and I-464), connecting different parts of the city and region. Travelers arriving at Norfolk International Airport (ORF) will find a rental car convenient for reaching their accommodations and navigating to sites like Greenbrier Mall or Ocean View Beach. Booking a rental car with your Chesapeake vacation package can enhance your travel experience.

Are Chesapeake vacation package hotels conveniently located?

Chesapeake vacation package hotels offer a range of locations, with many properties situated within a few miles of the city center.For example, Fairfield Inn and Suites By Marriott Chesapeake is about 3 miles from central Chesapeake, as are Residence Inn by Marriott Chesapeake Greenbrier and Comfort Suites Chesapeake - Norfolk. These hotels provide convenient access to local attractions. Some options, like YourSpace Hotels Chesapeake, are located further out, about 9 miles from central Chesapeake, offering a different experience.Consider your preferred proximity to specific attractions when choosing your Chesapeake vacation package.

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

Chesapeake vacation package hotels can place you within walking distance of shopping and dining options.For instance, TRU by Hilton Chesapeake, VA, Hilton Garden Inn Chesapeake/Greenbrier, and Courtyard by Marriott Chesapeake are all about a 5-minute walk from Greenbrier Mall, which offers various shops and restaurants. Additionally, Hampton Inn & Suites Chesapeake-Square Mall is about a 10-minute walk from Chesapeake Square Mall.Always check the map for your selected hotel to confirm walking routes to your preferred amenities.

Can I change or cancel my Chesapeake 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 Chesapeake 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 Chesapeake vacation packages?

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Chesapeake 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 Chesapeake?

To find last-minute vacation packages to Chesapeake, 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 Chesapeake vacation packages?

Free cancellation on a Chesapeake 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 Chesapeake vacation as a package or separately?

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Chesapeake 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 Chesapeake 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.

Chesapeake Vacations from $174

Book a Hotel + Flight or Car together to unlock savings

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Chesapeake Vacation

The Latest Chesapeake vacation packages

Budget Inn Norfolk Va

John Yancey Oceanfront Inn

Boardwalk Resort and Villas

Sea Scape Beach and Golf Villas

The Barclay Towers Resort Hotel

Where to stay in Chesapeake

Greenbrier

Deep Creek South

Greenbrier East

Greenbrier West

South Norfolk

Stay near popular Chesapeake attractions

Greenbrier Mall

Chesapeake Square Mall

Chesapeake Conference Center

Chesapeake City Park

Lake Drummond

Oak Grove Lake Park

Camelot Park

Chesapeake Veterans' Memorial

What to do in Chesapeake

Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin

City Cruises Norfolk: Signature Dinner Cruise

Buried Beneath the Boardwalk: Neptune Ghouls and Ghost Tours

Chesapeake Hotel Deals

Comfort Suites Chesapeake - Norfolk

YourSpace Hotels Chesapeake

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

Find the Best Chesapeake Vacation Packages

Things to do in and around Chesapeake

Find the best attractions near Chesapeake

Best time to go to Chesapeake

Tips to save on your trip to Chesapeake

Chesapeake Essential Information

More vacations you might like

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app