Title: Book the Best Chesapeake LUXURY Hotels - Upscale Hotels in Chesapeake, VA | Expedia.ca [Chesapeake Travel Guide](https://expedia.ca/Chesapeake.dx6612)[Hotels in Chesapeake](https://expedia.ca/Chesapeake-Hotels.d6612.Travel-Guide-Hotels)[Vacation Rentals in Chesapeake](https://expedia.ca/Chesapeake-Vacation-Rentals.d6612.Travel-Guide-VacationRentals)[Flights to Chesapeake](https://expedia.ca/Cheap-Flights-To-Chesapeake.d6612.Travel-Guide-Flights)[Chesapeake Car Rentals](https://expedia.ca/Car-Rentals-In-Chesapeake.d6612.Car-Rental-Guide)[Chesapeake Vacation Packages](https://expedia.ca/Chesapeake.d6612.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/481000/481121-Chesapeake-Square-Mall.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find luxury hotels in Chesapeake, VA ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](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) ![](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 Luxury Hotels Tonight [Oct 19 - Oct 20](https://www.expedia.ca/Hotel-Search?regionId=6612&startDate=2025-10-19&endDate=2025-10-20&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Oct 20 - Oct 21](https://www.expedia.ca/Hotel-Search?regionId=6612&startDate=2025-10-20&endDate=2025-10-21&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6612&startDate=2025-10-24&endDate=2025-10-26&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6612&startDate=2025-10-31&endDate=2025-11-02&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Top Chesapeake Luxury Hotels ![View from property](https://images.trvl-media.com/lodging/3000000/2180000/2178600/2178508/40b8c7ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2180000/2178600/2178508/bdd1b1a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/3000000/2180000/2178600/2178508/0f3f8b52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/3000000/2180000/2178600/2178508/c600575b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aloft Chesapeake Greenbrier East 8.4/10 Very good (1010) "Great place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wilson CA $157 CA $183 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chesapeake-Hotels-Aloft-Chesapeake.h2178508.Hotel-Information) ![Deluxe Room, 2 Double Beds (Smoke Free)](https://images.trvl-media.com/lodging/1000000/10000/2000/1927/a9448b44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee shop](https://images.trvl-media.com/lodging/1000000/10000/2000/1927/f763598b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/1000000/10000/2000/1927/c90a645b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/2000/1927/dc68bad5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Roof Inn Chesapeake Conference Center Chesapeake 7.0/10 Good (1006) "Clean rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Manuel CA $100 CA $117 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chesapeake-Hotels-Red-Roof-Inn-Chesapeake-Conference-Center.h1927.Hotel-Information) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/3000000/2210000/2201800/2201789/17a9ea67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, minibar, desk, iron/ironing board](https://images.trvl-media.com/lodging/3000000/2210000/2201800/2201789/6b87b9ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2210000/2201800/2201789/ed6b8b05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2210000/2201800/2201789/c054d0a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Chesapeake Greenbrier East 8.4/10 Very good (1009) "Breakfast was great and staff was very kind " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Toree CA $142 CA $166 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Chesapeake-Hotels-Hyatt-Place-Chesapeake.h2201789.Hotel-Information) ![Suite](https://images.trvl-media.com/lodging/1000000/10000/6600/6570/74e17a93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/1000000/10000/6600/6570/5aa674d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/6600/6570/222db243.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/6600/6570/059a327e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Suites Chesapeake - Norfolk Greenbrier East 8.4/10 Very good (1030) "Great check in and rooms are large and clean. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Adair CA $113 CA $133 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Chesapeake-Hotels-Comfort-Suites-Chesapeake-Norfolk.h6570.Hotel-Information) ![Studio, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/50000/41700/41684/f6f8453f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/41700/41684/282f4b4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/41700/41684/fa6f9366.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/50000/41700/41684/fd4e9688.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Extended Stay America Suites Chesapeake Crossways Blvd Greenbrier East 6.4/10 (1002) "Wonderful place to stay!!!!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matt CA $106 CA $125 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Chesapeake-Hotels-Extended-Stay-America-Suites-Chesapeake-Crossways-Blvd.h41684.Hotel-Information) ![Fridge, microwave, stovetop, dining tables](https://images.trvl-media.com/lodging/1000000/900000/893000/892957/bc1ccf91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/893000/892957/3145e2da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Laundry room](https://images.trvl-media.com/lodging/1000000/900000/893000/892957/852fcd60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![49-inch flat-screen TV with satellite channels, TV](https://images.trvl-media.com/lodging/1000000/900000/893000/892957/2e540dd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### InTown Suites Extended Stay Chesapeake VA – I-64/Crossway Blvd Greenbrier East 5.4/10 (649) "It was okay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kizzie [](https://www.expedia.ca/Chesapeake-Hotels-InTown-Suites-Extended-Stay-Chesapeake-VA-I-64.h892957.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/1000000/50000/43100/43064/f2e59564.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/50000/43100/43064/33d97aa9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/50000/43100/43064/65fd233d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served](https://images.trvl-media.com/lodging/1000000/50000/43100/43064/459552a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Chesapeake Greenbrier East 7.4/10 Good (584) "Great place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deandre CA $142 CA $166 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Chesapeake-Hotels-Courtyard-By-Marriott-Chesapeake.h43064.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=2025-11-02&endDate=2025-11-03®ionId=6612&adults=2&star=50&sort=RECOMMENDED&openPlayBack=true) ## Find out more about Chesapeake ### Chesapeakeand its attractions for luxury travelers Chesapeake, Virginia offers a delightful blend of natural beauty and refined experiences for luxury travellers. Begin your journey at the Great Dismal Swamp National Wildlife Refuge, where you can explore stunning landscapes filled with wildlife on a guided boat tour or hiking excursion, perfect for those with an adventurous spirit. Next, indulge in a day of golf at the prestigious Greenbrier Country Club, featuring a pristine course and superb amenities that ensure a relaxing afternoon of sport and leisure. For a taste of culture, visit the Chesapeake Planetarium, where you can enjoy captivating shows under the stars, followed by a stroll through the vibrant local art scene. A visit to the Chesapeake City Park is ideal for families, with its picturesque gardens and playgrounds, allowing for a leisurely picnic in a serene setting. Finally, don’t miss the exquisite dining experience at the renowned Bodega Restaurant, known for its innovative cuisine and intimate atmosphere, perfect for a romantic evening. Luxury travellers will find the best accommodations in the Greenbrier area, where upscale hotels provide attentive service and a wealth of amenities, ensuring a pampered stay as you explore the city's attractions. ### Find the best luxury hotels and resorts in Chesapeake For travelers seeking a touch of elegance in Chesapeake, Virginia, these luxury hotels offer exceptional amenities and a refined atmosphere for a memorable stay. [Delta Hotels by Marriott Chesapeake Norfolk](https://www.expedia.ca/Chesapeake-Hotels-Delta-Hotels-By-Marriott-Chesapeake-Norfolk.h6731.Hotel-Information) - **Why it's great for a luxury retreat:** The Delta Hotels by Marriott Chesapeake Norfolk stands out as a superb choice for luxury travelers, an excellent guest review rating of 8.6. With its prime location near a shopping district, guests can indulge in high-end retail experiences and enjoy the convenience of nearby attractions. The hotel features a sophisticated design, complemented by a rooftop garden perfect for relaxation and enjoying serene views. - **Other amenities:** Guests can take advantage of an indoor pool for leisurely swims, and a well-equipped fitness centre for maintaining their workout routines. The hotel also offers daily housekeeping, complimentary toiletries, and an accessible van parking facility. An on-site snack bar ensures that refreshments are never far away, while nearby golf courses provide an option for guests looking to enjoy a round in a picturesque setting. - **Nearby attractions:** Chesapeake Conference Center - 0.7 km, Greenbrier Mall - 2.4 km, Chesapeake City Park - 4.3 km ## Top Chesapeake Hotel Reviews ![Schooner Inn](//images.trvl-media.com/lodging/2000000/1720000/1711400/1711317/f35c64c2_y.jpg) ### Schooner Inn 10/10 Excellent "The staff was great. Rooms are big. " [](https://expedia.ca/Virginia-Beach-Hotels-Schooner-Inn.h1711317.Hotel-Information) ![Comfort Suites Chesapeake - Norfolk](//images.trvl-media.com/lodging/1000000/10000/6600/6570/74e17a93_y.jpg) ### Comfort Suites Chesapeake - Norfolk 10/10 Excellent "Good condition and excellent communication with the front desk " [](https://expedia.ca/Chesapeake-Hotels-Comfort-Suites-Chesapeake-Norfolk.h6570.Hotel-Information) ![Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)](//images.trvl-media.com/lodging/1000000/10000/5400/5363/c80e2694_y.jpg) ### Country Inn & Suites by Radisson, Virginia Beach (Oceanfront) 10/10 Excellent "The staff was very friendly and helpful. The room and facility were clean. It was a great hotel experience. " [](https://expedia.ca/Virginia-Beach-Hotels-Country-Inn-Suites-By-Radisson.h5363.Hotel-Information) ![Holiday Inn Va Beach-Oceanside (21st St) by IHG](//images.trvl-media.com/lodging/1000000/10000/4900/4857/9b6817bb_y.jpg) ### Holiday Inn Va Beach-Oceanside (21st St) by IHG 10/10 Excellent "A really nice room with an ocean view. At the front desk Lee and Rocky are Super stars. Erica from housekeeping did an excellent job." [](https://expedia.ca/Virginia-Beach-Hotels-Holiday-Inn-Oceanside-VA-Beach.h4857.Hotel-Information) ![Oceanfront Inn](//images.trvl-media.com/lodging/3000000/2100000/2094900/2094819/05b11887_y.jpg) ### Oceanfront Inn 10/10 Excellent "The staff was so professional and friendly. The room was clean and attractive. We had a great stay!" [](https://expedia.ca/Virginia-Beach-Hotels-Oceanfront-Inn.h2094819.Hotel-Information) ![Hilton Vacation Club Ocean Beach Club Virginia Beach](//images.trvl-media.com/lodging/2000000/1370000/1367400/1367330/b6b50f9a_y.jpg) ### Hilton Vacation Club Ocean Beach Club Virginia Beach 10/10 Excellent "I like the peace and quiet atmosphere. The room was neat." [](https://expedia.ca/Virginia-Beach-Hotels-Ocean-Beach-Club-By-Diamond-Resorts.h1367330.Hotel-Information) ![Holiday Inn & Suites Virginia Beach North Beach by IHG](//images.trvl-media.com/lodging/1000000/20000/16300/16268/631516bd_y.jpg) ### Holiday Inn & Suites Virginia Beach North Beach by IHG 10/10 Excellent "Great place to stay right on the beach." [](https://expedia.ca/Virginia-Beach-Hotels-Holiday-Inn-Suites-Virginia-Beach-North-Beach.h16268.Hotel-Information) ![Oceans 2700](//images.trvl-media.com/lodging/6000000/5480000/5479500/5479442/a7a4bc43_y.jpg) ### Oceans 2700 10/10 Excellent "I enjoyed a one night stay on a rainy September Saturday. The hotel was great. The building has been there for decades so it is old, but perfectly maintained, newer appliances and fixtures, immaculately clean. The room wasn't super big especially with two queen beds in, but big enough to shower sleep and chill. It's VB oceanfront so dozens of food beverage and shopping options within blocks. One block from the beach. Lots of convenience stores but only one full grocery store in the area and it's about three blocks away from this hotel so that was great. There's a small pool, barely any lobby to speak of or other common areas. Just a door to a balcony, the steps are outside as well but right next to the parking." [](https://expedia.ca/Virginia-Beach-Hotels-Oceans-2700.h5479442.Hotel-Information) ![Red Roof Inn Chesapeake Conference Center](//images.trvl-media.com/lodging/1000000/10000/2000/1927/a9448b44_y.jpg) ### Red Roof Inn Chesapeake Conference Center 10/10 Excellent "Clean rooms" [](https://expedia.ca/Chesapeake-Hotels-Red-Roof-Inn-Chesapeake-Conference-Center.h1927.Hotel-Information) ## Frequently asked questions ### Are you searching for a great accommodation for your luxury holiday in Chesapeake? > Use Expedia to help you arrange a flight to Norfolk Intl. Airport (ORF) airport or Newport News - Williamsburg Intl. Airport (PHF) airport, and then choose from a variety of places to stay that will deliver the luxury you want. Amenities are important when you plan a trip, so we make it easy to find what you want to make your stay special. If you want an upscale hotel with a spa, an indoor pool, or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Chesapeake has to offer. During your visit, you might want to enjoy the beaches and shopping which Chesapeake is known for. ### When can I expect good weather in Chesapeake? > Planning for the weather is an important factor for making your trip to Chesapeake a success, especially when you're splurging. The hottest months are usually July and August with an average temp of 77°F, while the coldest months are January and February with an average of 45°F. Average annual precipitation for Chesapeake is 54 inches. ### What's there to see and do in Chesapeake? > Enjoy Chesapeake and visit Greenbrier Mall, Chesapeake Conference Center, and Chesapeake Square Mall. If you have extra time while you're in the area, you might want to stop by Cahoon Plantation Golf Course and Chesapeake Golf Club. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [Hotels near Chesapeake Conference Center](https://www.expedia.ca/Chesapeake-Conference-Center-Hotels.0-l6083013-0.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Deep Creek South](https://www.expedia.ca/Deep-Creek-South-Chesapeake-Hotels-Adults-Only-Resorts.0-n553248635976473910-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Deep Creek South](https://www.expedia.ca/Deep-Creek-South-Chesapeake-Hotels-Romantic-Hotel.0-n553248635976473910-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Deep Creek South Hotels](https://www.expedia.ca/Deep-Creek-South-Chesapeake-Hotels.0-n553248635976473910-0.Travel-Guide-Filter-Hotels) - [Green Hotels in Virginia](https://www.expedia.ca/Destinations-In-Virginia-Green-Sustainable.0-0-d248-tGreenSustainable.Hotel-Filter-Destinations) - 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[Visit Greenbrier West](https://www.expedia.ca/Chesapeake-Greenbrier-West.dx553248635976480700) - [Children's Museum of Virginia](https://www.expedia.ca/Childrens-Museum-Of-Virginia-Portsmouth.d6083017.Vacation-Attraction) - [Commodore Theatre](https://www.expedia.ca/Commodore-Theatre-Portsmouth.d6301232.Vacation-Attraction) - [Douglas MacArthur Memorial](https://www.expedia.ca/Douglas-MacArthur-Memorial-Downtown-Norfolk.d6083029.Vacation-Attraction) - [Frank D Lawrence Stadium](https://www.expedia.ca/Frank-D-Lawrence-Stadium-Portsmouth.d6310280.Vacation-Attraction) - [Nauticus National Maritime Center](https://www.expedia.ca/Nauticus-National-Maritime-Center-Downtown-Norfolk.d6083061.Vacation-Attraction) - [Norfolk Vacations](https://www.expedia.ca/Norfolk.d2689.Destination-Travel-Guides) - [Visit Norfolk](https://www.expedia.ca/Norfolk.dx2689) - [Portsmouth Vacations](https://www.expedia.ca/Portsmouth.d9442.Destination-Travel-Guides) - [Uss Wisconsin BB-64](https://www.expedia.ca/USS-Wisconsin-BB-64-Downtown-Norfolk.d6241607.Vacation-Attraction) - [Waterside District](https://www.expedia.ca/Waterside-District-Downtown-Norfolk.d6171207.Vacation-Attraction) - [Avis Rental Cars in Norfolk](https://www.expedia.ca/Avis-Car-Rentals-In-Norfolk.d2689-c41.Car-Rental-Guide-Suppliers) - [Car rental Norfolk](https://www.expedia.ca/Car-Rentals-In-Norfolk.d2689.Car-Rental-Guide) - [Car rental Portsmouth](https://www.expedia.ca/Car-Rentals-In-Portsmouth.d9442.Car-Rental-Guide) - [Payless Rental Cars in Greenbrier East](https://www.expedia.ca/Payless-Car-Rentals-In-Greenbrier-East.d553248635976479827-c38.Car-Rental-Guide-Suppliers) - [Norfolk Vacation Rentals](https://www.expedia.ca/Norfolk-Vacation-Rentals.d2689.Travel-Guide-VacationRentals) - [Things to do in Norfolk](https://www.expedia.ca/Things-To-Do-In-Norfolk.d2689.Travel-Guide-Activities) - [Things to do in Portsmouth](https://www.expedia.ca/Things-To-Do-In-Portsmouth.d9442.Travel-Guide-Activities) - [Book Luxury Hotels in Chesapeake on Expedia.com](https://www.expedia.com/Chesapeake-Hotels-Luxury-Hotel.0-0-d6612-tLuxuryHotel.Travel-Guide-Filter-Hotels)