Title: Book Chesapeake Vacation Packages - 2026 | Expedia.com [Chesapeake Travel Guide](https://expedia.com/Chesapeake.dx6612)[Hotels in Chesapeake](https://expedia.com/Chesapeake-Hotels.d6612.Travel-Guide-Hotels)[Vacation Rentals in Chesapeake](https://expedia.com/Chesapeake-Vacation-Rentals.d6612.Travel-Guide-VacationRentals)[Flights to Chesapeake](https://expedia.com/Cheap-Flights-To-Chesapeake.d6612.Travel-Guide-Flights)[Things to do in Chesapeake](https://expedia.com/Things-To-Do-In-Chesapeake.d6612.Travel-Guide-Activities)[Car Rentals in Chesapeake](https://expedia.com/Car-Rentals-In-Chesapeake.d6612.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6612/a9713a83-9e8c-48e1-a2a0-408a1c201fa4.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chesapeake Vacations from $478 ## Book a Hotel + Flight or Car together to unlock savings Photo by Kaylee Spinhirn - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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](https://www.expedia.com/Greenbrier-Mall-Greenbrier-East.d6273847.Vacation-Attraction), [Oak Grove Lake Park](https://www.expedia.com/Oak-Grove-Lake-Park-Greenbrier-West.d6301205.Vacation-Attraction) and [Chesapeake City Park](https://www.expedia.com/Chesapeake-City-Park-Greenbrier-East.d6083011.Vacation-Attraction) 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. ![Boardwalk Resort and Villas](https://images.trvl-media.com/lodging/1000000/920000/910400/910351/7bb2cf2f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Boardwalk Resort and Villas Northeast Virginia Beach Save 100% on your flight $478 per person May 8 - May 11 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Norfolk (ORF) 8.6/10 Excellent! (1,003 reviews) Staff was very helpful and communicative Reviewed on Jan 29, 2026 ![Sanderling Resort Residences](https://images.trvl-media.com/lodging/100000000/99930000/99920100/99920084/26b95408_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sanderling Resort Residences Save 100% on your flight $2,514 per person Apr 21 - Apr 25 found 1 day ago Roundtrip flight included Boston (BOS) to Norfolk (ORF) No reviews ![The Sanderling](https://images.trvl-media.com/lodging/1000000/920000/913900/913817/c90c4d85_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Sanderling Save 100% on your flight $1,127 per person Apr 21 - Apr 25 found 1 day ago Roundtrip flight included Boston (BOS) to Norfolk (ORF) 8.8/10 Excellent! (523 reviews) The elevator was broken. We were told that had been struck by lightning. I was also told that it had been broken for one year. They have three floors almost 2 of the buildings and I think two on the other, but I don’t know if they meant elevators in the building that we were in or every single one wasn’t clarified also told that they were having a New Year’s Eve celebration. Nothing was held in the lobby as previously expected the restaurant on site closed at 9 PM New Year’s Eve and we were rushed like you wouldn’t believe for six course meal that cost $300. Reviewed on Jan 7, 2026 ![Pamlico Station Edgecamp](https://images.trvl-media.com/lodging/103000000/102110000/102108500/102108447/7849d4bb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pamlico Station Edgecamp South Rodanthe Save 100% on your flight $823 per person May 8 - May 12 found 14 hours ago Roundtrip flight included Newark Liberty Intl. Airport (EWR) to Norfolk (ORF) 9.4/10 Exceptional! (19 reviews) beautiful room with very responsive concierge Reviewed on Jan 15, 2026 ![Hampton Inn & Suites Newport News (Oyster Point)](https://images.trvl-media.com/lodging/1000000/30000/21100/21074/1e9dfcd1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hampton Inn & Suites Newport News (Oyster Point) Central Newport News $527 per person Apr 25 - May 2 found 20 hours ago Roundtrip flight included New York (JFK) to Norfolk (ORF) 8.8/10 Excellent! (565 reviews) The front desk staff was courteous and friendly. The room had a smell but seemed clean. Breakfast was also good. Reviewed on Jan 8, 2026 Don't see what you're looking for? See all available trips from Columbus to Chesapeake [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-11/2026-03-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PHF&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Where to stay in Chesapeake Find the best Chesapeake areas and neighborhoods for the activities you enjoy most. [Learn more about Chesapeake](https://expedia.com/Chesapeake.dx6612) ![Silhouettes of trees in Great Dismal Swamp. Virginia, United States.](https://images.trvl-media.com/place/553248635976479827/3e7f7160-d17f-4047-85a3-7e12c732b1a8.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Greenbrier East 1 out of top 10 points of interest in this area 4/5(438 area reviews) While visiting Greenbrier East, you might make a stop by sights like Greenbrier Mall and Jillian's Billiards. [Find hotel + flight trips in Greenbrier East](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Greenbrier%20East&DestID=553248635976479827&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![1.5 miles around. No swimming. But a playground for the kiddos, dog friendly and tons of fishing spots :) ](https://images.trvl-media.com/place/6612/a9713a83-9e8c-48e1-a2a0-408a1c201fa4.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### 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. [Find hotel + flight trips in Greenbrier](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Greenbrier&DestID=946137804512284672&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Traveling south on the intracostal waterway. great bridge va.](https://images.trvl-media.com/place/6612/7937059d-5412-4b6d-aa49-26aec8b431f3.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Greenbrier West 3.5/5(49 area reviews) If you're spending some time in Greenbrier West, Chesapeake Arboretum and Bowlero Chesapeake are top sights worth seeing. [Find hotel + flight trips in Greenbrier West](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Greenbrier%20West&DestID=553248635976480700&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Newport News, Virginia, USA](https://images.trvl-media.com/place/553248635976388783/200cad18-a893-4842-a3b9-359f8cc97e65.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### 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. [Find hotel + flight trips in South Norfolk](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=South%20Norfolk&DestID=553248635976388783&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![scenes around chesapeak bay virginia beach](https://images.trvl-media.com/place/553248635976473375/524310d1-0742-437a-81c1-741d1bf30d85.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Great Bridge 1 out of top 10 points of interest in this area If you're spending some time in Great Bridge, Chesapeake City Hall and Cahoon Plantation Golf Course are top sights worth seeing. [Find hotel + flight trips in Great Bridge](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Great%20Bridge&DestID=553248635976473375&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ### Discover the most popular places to visit in Chesapeake ![Greenbrier Mall](https://images.trvl-media.com/place/6273847/920d6124-d998-482b-9bd7-35767b65c694.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Greenbrier Mall 4/5(260 reviews) You can browse for the perfect souvenirs at Greenbrier Mall during your visit to Chesapeake. Stroll along the beautiful beaches or attend a sporting event in the area. [](https://expedia.com/Greenbrier-Mall-Greenbrier.d6273847.Vacation-Attraction) ![Chesapeake Square Mall](https://images.trvl-media.com/place/6211311/3ce2bef9-a58d-480e-be7c-1f8f010c5d82.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chesapeake Square Mall 4/5(76 reviews) You can find the perfect gifts to bring home at Chesapeake Square Mall during your trip to Chesapeake. Discover the top-notch restaurants and acclaimed theater scene in this family-friendly area. [](https://expedia.com/Chesapeake-Square-Mall-Western-Branch-North.d6211311.Vacation-Attraction) ![Chesapeake Conference Center](https://images.trvl-media.com/place/6083013/1d91b5e2-338a-4532-a2ac-6556125f6d26.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chesapeake Conference Center After visiting Chesapeake Conference Center, make a plan to see the other sights and activities in Chesapeake. Experience the area's great live music and acclaimed theater scene. [](https://expedia.com/Chesapeake-Conference-Center-Chesapeake.d6083013.Vacation-Attraction) ### What to do in Chesapeake ![View of the water and the Spirit of Norfolk Dinner Cruise ship](https://mediaim.expedia.com/localexpert/174659/794d9e61-87fc-4a64-b0b9-9b590737e3a7.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### City Cruises Norfolk: Signature Dinner Cruise $139 per adult **76%** of travellers recommend [](https://expedia.com/things-to-do/city-cruises-norfolk-signature-dinner-cruise.a174659.activity-details) ![Ziplining and Climbing at The Adventure Park at Virginia Aquarium](https://mediaim.expedia.com/localexpert/46124400/0fabf6da-5814-4172-9b03-94f389f62573.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Ziplining and Climbing at The Adventure Park at Virginia Aquarium $64 per adult [](https://expedia.com/things-to-do/ziplining-and-climbing-at-the-adventure-park-at-virginia-aquarium.a46124400.activity-details) ![Visit Norfolk's Perk Up Pass](https://mediaim.expedia.com/localexpert/47153116/cebb6dd9-72f3-417c-88da-f9e725038575.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Visit Norfolk's Perk Up Pass $17 per adult [](https://expedia.com/things-to-do/visit-norfolks-perk-up-pass.a47153116.activity-details) [See all activities in Chesapeake](https://expedia.com/things-to-do/search?rid=6612) ## Chesapeake Hotel Deals ![Wingate by Wyndham Chesapeake](https://images.trvl-media.com/lodging/2000000/1520000/1513300/1513238/d607b035_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Wingate by Wyndham Chesapeake 817 Greenbrier Circle Chesapeake VA Fully refundableReserve now, pay when you stay $77 nightly $90 total Feb 22 - Feb 23 Total with taxes and fees 7.8/10 Good! (1,008 reviews) The room was spotless and the top notch Reviewed on Feb 9, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F22%2F2026&endDate=2%2F23%2F2026&selected=1513238&PinnedHotelID=1513238&HadPinnedHotel=true®ionId=6612) ![Comfort Suites Chesapeake - Norfolk](https://images.trvl-media.com/lodging/1000000/10000/6600/6570/74e17a93_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Comfort Suites Chesapeake - Norfolk 1550 Crossways Blvd Chesapeake VA Fully refundableReserve now, pay when you stay $80 nightly $94 total Feb 21 - Feb 22 Total with taxes and fees 8.6/10 Excellent! (1,012 reviews) Very attentive and friendly staff. Clean. Reviewed on Feb 9, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F21%2F2026&endDate=2%2F22%2F2026&selected=6570&PinnedHotelID=6570&HadPinnedHotel=true®ionId=6612) ![Fairfield Inn and Suites By Marriott Chesapeake](https://images.trvl-media.com/lodging/1000000/20000/16100/16036/234312b3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Fairfield Inn and Suites By Marriott Chesapeake 1560 Crossways Blvd Chesapeake VA Fully refundableReserve now, pay when you stay $85 nightly $100 total Feb 22 - Feb 23 Total with taxes and fees 8.8/10 Excellent! (1,002 reviews) Really nice front desk crew and all of the workers go out of the way to make you feel welcome. My 3rd stay here, and is my choice when staying in Chesapeake. Reviewed on Feb 8, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F22%2F2026&endDate=2%2F23%2F2026&selected=16036&PinnedHotelID=16036&HadPinnedHotel=true®ionId=6612) [See all 3,400 properties in Chesapeake](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F12%2F2026&endDate=2%2F13%2F2026®ionId=6612) 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](https://www.expedia.com/Greenbrier-Mall-Greenbrier-East.d6273847.Vacation-Attraction), which offers a variety of stores and entertainment. [Chesapeake Square Mall](https://www.expedia.com/Chesapeake-Square-Mall-Western-Branch-North.d6211311.Vacation-Attraction) 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](https://www.expedia.com/Harbor-Park-Norfolk.d6083037.Vacation-Attraction), where you can catch an exciting game and soak in the energizing sports vibes. For a night of live music, head to [The NorVa](https://www.expedia.com/The-NorVa-Downtown-Norfolk.d553248621532661647.Vacation-Attraction), a fantastic venue filled with entertainment energy. Enjoy relaxation and nature at [Oak Grove Lake Park](https://www.expedia.com/Oak-Grove-Lake-Park-Greenbrier.d6301205.Vacation-Attraction), perfect for unwinding. **Adventure** Experience the thrill of arcade games at [Jillian's Billiards](https://www.expedia.com/Jillians-Billiards-Greenbrier-East.d553248621532661654.Vacation-Attraction) 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: ](https://www.expedia.com/Norfolk-State-University-Norfolk.d6083069.Vacation-Attraction)** 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: ](https://www.expedia.com/Norfolk-Scope-Downtown-Norfolk.d6083067.Vacation-Attraction)** 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: ](https://www.expedia.com/Regent-University-Virginia-Beach.d553248635056398836.Vacation-Attraction)** 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](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)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](https://www.expedia.com/Portlock-Galleries-At-SoNo-Chesapeake.d553248621532661656.Vacation-Attraction), [Jillians Billiards](https://www.expedia.com/Jillians-Billiards-Greenbrier-East.d553248621532661654.Vacation-Attraction) and [Chesapeake City Park](https://www.expedia.com/Chesapeake-City-Park-Greenbrier-East.d6083011.Vacation-Attraction) | ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations 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[](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click) ![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Chesapeake vacation package cost? ### What are the cheapest months to go to Chesapeake? ### How many days is enough for Chesapeake? ### Is it worth booking a vacation package to Chesapeake? ### How to find the best Chesapeake package deals? ### Is it cheaper to book a Chesapeake vacation as a package? ### When to book a vacation package to Chesapeake? ### How to plan a trip to Chesapeake? > 1. Choose when to get away: Check your diary and get your bags packed. Your favorite time of year and the type of activities on offer will also help you decide when to escape to Chesapeake. > 2. Figure out your budget: Make sure you have enough money to pay for everything from transportation and dining out to activities and flights. Your hotel will likely be the biggest expense during your trip to Chesapeake. > 3. Use Expedia's [trip planning tool](https://www.expedia.com/why/trip-planning) to discover Chesapeake: Research every aspect of your trip to Chesapeake with this handy planner. Invite family or friends to collaborate on a group trip, search for hotels or things to do and make bookings. > 4. Determine how many days away: Start by making a list of all the activities and attractions you want to experience in Chesapeake. Then, estimate how long you'll need for each, as well as any travel time. > 5. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to find a Chesapeake vacation package that brings all your bookings together. > 6. Add on experiences and excursions: Take a look at our dedicated travel guide to find some fun [things to do in Chesapeake](https://www.expedia.com/Things-To-Do-In-Chesapeake.d6612.Travel-Guide-Activities). Book tickets or make reservations before you go to save time and avoid the stress of looking for activities once you arrive. ### Does Expedia offer Book Now, Pay Later Chesapeake vacation packages? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - More ways to book - [Hotels near Oak Grove Lake Park ](https://www.expedia.com/Oak-Grove-Lake-Park-Hotels.0-l6301205-0.Travel-Guide-Filter-Hotels) - [Hotels near Greenbrier West ](https://www.expedia.com/Greenbrier-West-Chesapeake-Hotels.0-n553248635976480700-0.Travel-Guide-Filter-Hotels) - [Norfolk Hotels ](https://www.expedia.com/Norfolk-Hotels.d2689.Travel-Guide-Hotels) - [Hotels near Cahoon Plantation Golf Course ](https://www.expedia.com/Cahoon-Plantation-Golf-Course-Hotels.0-l6083003-0.Travel-Guide-Filter-Hotels) - [Gay friendly Hotels in Deep Creek South ](https://www.expedia.com/Deep-Creek-South-Chesapeake-Hotels-LGBT-Welcoming-Hotel.0-n553248635976473910-0-tLGBTWelcomingHotel.Travel-Guide-Filter-Hotels) - 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