Title: Book the Best Chesapeake Bay ALL INCLUSIVE Resorts and Hotels | Expedia.ca [Chesapeake Bay Travel Guide](https://expedia.ca/Chesapeake-Bay.dx6056980)[Hotels in Chesapeake Bay](https://expedia.ca/Chesapeake-Bay-Hotels.d6056980.Travel-Guide-Hotels)[Vacation Rentals in Chesapeake Bay](https://expedia.ca/Chesapeake-Bay-Vacation-Rentals.d6056980.Travel-Guide-VacationRentals)[Flights to Chesapeake Bay](https://expedia.ca/Cheap-Flights-To-Chesapeake-Bay.d6056980.Travel-Guide-Flights)[Things to do in Chesapeake Bay](https://expedia.ca/Things-To-Do-In-Chesapeake-Bay.d6056980.Travel-Guide-Activities)[Chesapeake Bay Car Rentals](https://expedia.ca/Car-Rentals-In-Chesapeake-Bay.d6056980.Car-Rental-Guide)[Chesapeake Bay Vacation Packages](https://expedia.ca/Chesapeake-Bay.d6056980.Destination-Travel-Guides) ![Virginia which includes a statue or sculpture, a high-rise building and modern architecture](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/33000/33013-Town-Point-Park.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find All Inclusive Resorts and Hotels in Chesapeake Bay ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Chesapeake Bay All Inclusive Resorts and Hotels Tonight [Sep 27 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=6056980&startDate=2025-09-27&endDate=2025-09-28&adults=2&amenities=ALL_INCLUSIVE&mealPlan=ALL_INCLUSIVE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 28 - Sep 29](https://www.expedia.ca/Hotel-Search?regionId=6056980&startDate=2025-09-28&endDate=2025-09-29&adults=2&amenities=ALL_INCLUSIVE&mealPlan=ALL_INCLUSIVE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6056980&startDate=2025-10-03&endDate=2025-10-05&adults=2&amenities=ALL_INCLUSIVE&mealPlan=ALL_INCLUSIVE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6056980&startDate=2025-10-10&endDate=2025-10-12&adults=2&amenities=ALL_INCLUSIVE&mealPlan=ALL_INCLUSIVE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chesapeake Bay All Inclusive Resorts and Hotels ![Indoor pool, outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/870000/864100/864071/683f098a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/870000/864100/864071/20186df7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/870000/864100/864071/f6ae164f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/870000/864100/864071/8cd2f5ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Vacation Club The Historic Powhatan Williamsburg Williamsburg 9.0/10 Wonderful (3101) "Wonderful place to stay. " CA $97 CA $150 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Williamsburg-Hotels-The-Historic-Powhatan-Resort-By-Diamond-Resorts.h864071.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/1000000/60000/58700/58664/af2bbde8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, 2 outdoor pools, open 7 AM to 11 PM, pool umbrellas](https://images.trvl-media.com/lodging/1000000/60000/58700/58664/289ecf29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/60000/58700/58664/13a680bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/58700/58664/2c77360c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Marriott's Manor Club at Ford's Colony Williamsburg 9.2/10 Wonderful (1004) "The suites are perfect for our annual stays there with friends. " CA $166 CA $189 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Williamsburg-Hotels-Marriotts-Manor-Club-At-Fords-Colony.h58664.Hotel-Information) ![Indoor pool, 2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/900000/890500/890486/6000a351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/900000/890500/890486/585cd9b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/890500/890486/7c147ef6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/890500/890486/af06ef71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Regency Chesapeake Bay Cambridge 8.8/10 Excellent (1010) "Beautiful place" CA $266 CA $369 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Cambridge-Hotels-Hyatt-Regency-Chesapeake-Bay.h890486.Hotel-Information) ![Indoor pool, outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/1000000/430000/425200/425163/c1ddc325.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Suite, 2 Bedrooms, Balcony | Private kitchen](https://images.trvl-media.com/lodging/1000000/430000/425200/425163/8c4f5697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mini-golf](https://images.trvl-media.com/lodging/1000000/430000/425200/425163/aa5d9a1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/430000/425200/425163/bc5aa280.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Club Wyndham Kingsgate Williamsburg 8.8/10 Excellent (1014) "great as a vacation lodging option!" [](https://www.expedia.ca/Williamsburg-Hotels-Club-Wyndham-Kingsgate.h425163.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/870000/863100/863025/3f11083f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![32-inch TV with cable channels, fireplace, DVD player](https://images.trvl-media.com/lodging/1000000/870000/863100/863025/c9457bc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/1000000/870000/863100/863025/5c1dbbd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, in-room safe, individually decorated](https://images.trvl-media.com/lodging/1000000/870000/863100/863025/0c67ffdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Vacation Club Greensprings Williamsburg Williamsburg 8.4/10 Very good (1022) "Great place to stay at." CA $101 CA $155 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Williamsburg-Hotels-Greensprings-Vacation-Resort.h863025.Hotel-Information) ![On the beach, beach bar](https://images.trvl-media.com/lodging/2000000/1370000/1367400/1367330/b6b50f9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1370000/1367400/1367330/6a8758c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/2000000/1370000/1367400/1367330/6df441de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1370000/1367400/1367330/ad2a824f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Vacation Club Ocean Beach Club Virginia Beach Northeast Virginia Beach 8.4/10 Very good (1137) "Enjoyable stay would do again for fire, very convenient with fun activities food and view " CA $135 CA $198 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Virginia-Beach-Hotels-Ocean-Beach-Club-By-Diamond-Resorts.h1367330.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/18000000/17240000/17230900/17230833/23306f7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![12 restaurants, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/18000000/17240000/17230900/17230833/14c720e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment rooms, sauna, hot tub, steam room, body treatments](https://images.trvl-media.com/lodging/18000000/17240000/17230900/17230833/bb984392.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/18000000/17240000/17230900/17230833/36b45d4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### MGM National Harbor Resort & Casino Oxon Hill 8.6/10 Excellent (1004) "Staff was pleasant. Great hotel" CA $458 CA $581 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/College-Park-Hotels-MGM-National-Harbor-Resort-Casino.h17230833.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/3000000/2810000/2804100/2804098/12d1a93d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/3000000/2810000/2804100/2804098/w3995h2663x0y4-246ea4b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/3000000/2810000/2804100/2804098/67944d18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2810000/2804100/2804098/acfd87f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aloft BWI Baltimore Washington International Airport Linthicum Heights 8.2/10 Very good (1310) "Great place to stay" CA $128 CA $145 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Baltimore-Hotels-Aloft-BWI-Baltimore-Washington-International-Airport.h2804098.Hotel-Information) ![Rooftop terrace](https://images.trvl-media.com/lodging/1000000/10000/9400/9379/50c62e4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Double Beds, Harbour View](https://images.trvl-media.com/lodging/1000000/10000/9400/9379/b3b36482.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/1000000/10000/9400/9379/f1bf4ef3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9400/9379/53ebad59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Regency Baltimore Inner Harbor Inner Harbor 8.4/10 Very good (1825) "Super friendly staff, clean and lovely hotel! Great location, would definitely stay here again." CA $235 CA $277 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Baltimore-Hotels-Hyatt-Regency-Baltimore-Inner-Harbor.h9379.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1780000/1777200/1777196/92ceb02c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1780000/1777200/1777196/a021b7fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/2000000/1780000/1777200/1777196/6a709e04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/2000000/1780000/1777200/1777196/7074a3e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gaylord National Resort & Convention Center Fort Washington 8.8/10 Excellent (1011) "Stayed there many times. Everything was exceptional." CA $375 CA $480 total includes taxes & fees Oct 10 - Oct 11 [](https://www.expedia.ca/College-Park-Hotels-Gaylord-National-Resort-Convention-Center.h1777196.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-11&endDate=2025-10-12®ionId=6056980&adults=2&mealPlan=ALL_INCLUSIVE&sort=RECOMMENDED&openPlayBack=true) ## Find out more about Chesapeake Bay ### Discover top Chesapeake Bay attractions Chesapeake Bay offers a wealth of activities perfect for families and travellers seeking all-inclusive experiences. Begin your adventure at the historic town of Annapolis, where you can explore the United States Naval Academy and wander the charming streets lined with 18th-century buildings. After a day of exploration, indulge in fresh seafood at local eateries; many all-inclusive hotels offer a variety of dining options from casual bites to gourmet experiences featuring the bay's famous blue crabs. For nature lovers, a visit to the Chesapeake Bay Environmental Center allows for kayaking and birdwatching, with some resorts providing guided tours as part of their packages. Families can enjoy a day at Sandy Point State Park, where sandy beaches and picnic areas await, often included in all-inclusive deals that provide equipment for a perfect day out. Lastly, consider staying in the picturesque town of St. Michaels, known for its quaint shops and waterfront views, where all-inclusive hotels might offer spa services and evening entertainment, ensuring a relaxing retreat after a day of adventure. With attentive service and an array of activities and dining options, Chesapeake Bay is a delightful choice for those seeking both relaxation and exploration. ## Top Chesapeake Bay Hotel Reviews ![Hilton Vacation Club The Historic Powhatan Williamsburg](//images.trvl-media.com/lodging/1000000/870000/864100/864071/683f098a_y.jpg) ### Hilton Vacation Club The Historic Powhatan Williamsburg 10/10 Excellent "Clean and well maintained. My only issue is the extra resort fee of $50 I had to pay and did not use any of the resort amenities because it was a very short stay to go to Busch Gardens." 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