HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit

Make a self catering cottage or holiday rental in Chesapeake Bay, Maryland your home away from home

Chesapeake Bay is a 180-mile long estuary running down between the coast of Maryland and Virginia. It has many inlets and more than 150 rivers feeding it before it finally reaches the Atlantic Ocean. The bay area is noted for its scenic natural beauty and its world-famous crabs and oysters.

Things to Do in Chesapeake Bay, Maryland

Chesapeake Bay is famous for its fishing. Rockfish, also known as striped bass, blue crabs, clams and eels can all be caught here and visitors will get the chance to sample the fresh seafood at the many restaurants in the area around their Chesapeake Bay holiday rentals. Enjoy the beach and boardwalk at Ocean City or spend a day driving around the scenic backwaters discovering the diverse wildlife. You can take a scenic hot air balloon flight to see the vast Chesapeake Bay from the air or book a place on a sightseeing boat tour to see more of the area's natural beauty and wildlife at close quarters. Several places offer kayaking trips and canoes for hire to paddle the shallow waterways. Museums and art galleries abound in the area along with state parks.

Places to Visit Around Chesapeake Bay, Maryland

Chestertown is well worth visiting to see its farmers' market and the Washington College campus buildings. Cambridge is one of the oldest towns in Maryland. It has several museums including the fascinating Brannock Maritime Museum and the Richardson Maritime Museum. Nearby are Hooper's Island and Taylor's Island, traditionally the home of local watermen. Taylor's Island has 18th century churches, schools and a historic cannon captured from the British in the war of 1812. Another place of interest to visit is Annapolis, the capital of Maryland which has old world charm in its historic architecture and is home to the U.S. Naval Academy.

Weather in Chesapeake Bay, Maryland

Chesapeake Bay enjoys hot humid summers and cold winters tempered by the proximity to the water. In summer, daytime highs average 31°C (88°F) while in winter temperatures are generally just above freezing by day and below freezing at night although the bay waters rarely freeze. Showers can be expected in any month. Spring is a beautiful time to visit and enjoy the cherry blossom and spring flowers. Autumn sees the trees change to vivid orange, red and gold heralding cooler months ahead.

Travel to Chesapeake Bay, Maryland

Chesapeake Bay holiday rentals can be reached from the Washington National (DCA) Airport which is just outside downtown Washington D.C. or the Baltimore-Washington International (BWI) Airport which is about 40 miles further north. Both airports are serviced by major airlines from many national and international destinations making the area very easy to reach by air. A car is recommended for driving to your Chesapeake Bay vacation home and for exploring the area.

  • Showing 1-50 of 76
Additional service fee may apply.
  View Map Map
    Wonderful! 4.8/5
    (38 reviews)
    avg/night
    • 2 BR
    • 1 BA
    • Sleeps 5
    House #7080944
    38
    Viewed 78 times in the last 48 hours
      Exceptional! 5.0/5
      (6 reviews)
      avg/night
      • 2 BR
      • 1 BA
      • Separate Toilets
      • Sleeps 5
      Cottage #844888vb
      6
      Viewed 51 times in the last 48 hours
        Exceptional! 5.0/5
        (20 reviews)
        avg/night
        • 2 BR
        • 2 BA
        • Sleeps 5
        Cottage #608459vb
        20
        Viewed 42 times in the last 48 hours
          Exceptional! 5.0/5
          (25 reviews)
          avg/night
          • 4 BR
          • 3 BA
          • Sleeps 8
          House #684953vb
          25
          Viewed 60 times in the last 48 hours
            Exceptional! 5.0/5
            (5 reviews)
            avg/night
            • 3 BR
            • 2 BA
            • Sleeps 6
            Cottage #4230519
            5
            Viewed 55 times in the last 48 hours
              Wonderful! 4.8/5
              (17 reviews)
              avg/night
              • 3 BR
              • 3 BA
              • Separate Toilet
              • Sleeps 9
              House #572361vb
              17
              Viewed 10 times in the last 48 hours
                • 2 BR
                • 2 BA
                • Sleeps 5
                Cottage #844892vb
                0
                Viewed 40 times in the last 48 hours
                  Wonderful! 4.9/5
                  (13 reviews)
                  avg/night
                  • 3 BR
                  • 2 BA
                  • Sleeps 8
                  House #833414vb
                  13
                  Viewed 28 times in the last 48 hours
                    avg/night
                    • 3 BR
                    • 2 BA
                    • Separate Toilet
                    • Sleeps 6
                    Cottage #743920vb
                    4
                    Viewed 23 times in the last 48 hours
                      Exceptional! 5.0/5
                      (17 reviews)
                      avg/night
                      • 3 BR
                      • 2 BA
                      • Separate Toilet
                      • Sleeps 8
                      Cottage #503705vb
                      17
                      Viewed 19 times in the last 48 hours
                        Wonderful! 4.8/5
                        (25 reviews)
                        avg/night
                        • 2 BR
                        • 1 BA
                        • Separate Toilet
                        • Sleeps 6
                        House #431733vb
                        25
                        Viewed 12 times in the last 48 hours
                          Wonderful! 4.9/5
                          (12 reviews)
                          avg/night
                          • 3 BR
                          • 1 BA
                          • Separate Toilet
                          • Sleeps 10
                          Cottage #738202vb
                          12
                          Viewed 49 times in the last 48 hours
                            Exceptional! 5.0/5
                            (15 reviews)
                            avg/night
                            • 4 BR
                            • 3 BA
                            • Separate Toilet
                            • Sleeps 10
                            Townhome #733103vb
                            15
                            Viewed 20 times in the last 48 hours
                              Wonderful! 4.9/5
                              (12 reviews)
                              avg/night
                              • 2 BR
                              • 1 BA
                              • Sleeps 6
                              Cottage #694511vb
                              12
                              Viewed 18 times in the last 48 hours
                                Wonderful! 4.8/5
                                (37 reviews)
                                avg/night
                                • 2 BR
                                • 2 BA
                                • Sleeps 6
                                Cottage #122453
                                37
                                Viewed 33 times in the last 48 hours
                                  Exceptional! 5.0/5
                                  (8 reviews)
                                  avg/night
                                  • 3 BR
                                  • 3 BA
                                  • Separate Toilet
                                  • Sleeps 10
                                  Chateau / Country House #677979vb
                                  8
                                  Viewed 10 times in the last 48 hours
                                    • 2 BR
                                    • 2 BA
                                    • Sleeps 6
                                    House #702464vb
                                    11
                                      Excellent! 4.4/5
                                      (21 reviews)
                                      avg/night
                                      • 3 BR
                                      • 1 BA
                                      • Sleeps 6
                                      Cottage #407081vb
                                      21
                                      Viewed 8 times in the last 48 hours
                                        Wonderful! 4.9/5
                                        (10 reviews)
                                        avg/night
                                        • 3 BR
                                        • 1 BA
                                        • Separate Toilet
                                        • Sleeps 8
                                        House #571411vb
                                        10
                                        Viewed 12 times in the last 48 hours
                                          • 4 BR
                                          • 1 BA
                                          • Sleeps 8
                                          House #3589032
                                          4
                                          Viewed 15 times in the last 48 hours
                                            Exceptional! 5.0/5
                                            (12 reviews)
                                            avg/night
                                            • 5 BR
                                            • 5 BA
                                            • Sleeps 14
                                            Lodge #665175vb
                                            12
                                            Viewed 41 times in the last 48 hours
                                              Wonderful! 4.9/5
                                              (19 reviews)
                                              avg/night
                                              • 3 BR
                                              • 1 BA
                                              • Sleeps 6
                                              House #429964vb
                                              19
                                              Viewed 13 times in the last 48 hours
                                                Wonderful! 4.9/5
                                                (8 reviews)
                                                avg/night
                                                • 4 BR
                                                • 3 BA
                                                • Separate Toilet
                                                • Sleeps 8
                                                House #458295vb
                                                8
                                                Viewed 27 times in the last 48 hours
                                                  Exceptional! 5.0/5
                                                  (10 reviews)
                                                  avg/night
                                                  • 3 BR
                                                  • 2 BA
                                                  • Sleeps 6
                                                  House #220506vb
                                                  10
                                                  Viewed 19 times in the last 48 hours
                                                    Wonderful! 4.9/5
                                                    (10 reviews)
                                                    avg/night
                                                    • 3 BR
                                                    • 2 BA
                                                    • Sleeps 9
                                                    Apartment #409821vb
                                                    10
                                                    Viewed 28 times in the last 48 hours
                                                      Wonderful! 4.8/5
                                                      (22 reviews)
                                                      avg/night
                                                      • 3 BR
                                                      • 1 BA
                                                      • Sleeps 6
                                                      Cottage #418738vb
                                                      22
                                                      Viewed 6 times in the last 48 hours
                                                        Wonderful! 4.9/5
                                                        (15 reviews)
                                                        avg/night
                                                        • 3 BR
                                                        • 1 BA
                                                        • Separate Toilet
                                                        • Sleeps 6
                                                        House #706523vb
                                                        15
                                                        Viewed 20 times in the last 48 hours
                                                          avg/night
                                                          • 3 BR
                                                          • 2 BA
                                                          • Separate Toilet
                                                          • Sleeps 6
                                                          House #859089vb
                                                          0
                                                          Viewed 5 times in the last 48 hours
                                                            Excellent! 4.7/5
                                                            (15 reviews)
                                                            avg/night
                                                            • 4 BR
                                                            • 2 BA
                                                            • Sleeps 9
                                                            House #410948vb
                                                            15
                                                            Viewed 48 times in the last 48 hours
                                                              avg/night
                                                              • 4 BR
                                                              • 3 BA
                                                              • Sleeps 8
                                                              House #3589033
                                                              0
                                                              Viewed 15 times in the last 48 hours
                                                                Wonderful! 4.8/5
                                                                (8 reviews)
                                                                avg/night
                                                                • 3 BR
                                                                • 1 BA
                                                                • Sleeps 6
                                                                House #189398vb
                                                                8
                                                                Viewed 25 times in the last 48 hours
                                                                  avg/night
                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • Sleeps 8
                                                                  House #3953062
                                                                  3
                                                                  Viewed 22 times in the last 48 hours
                                                                    Exceptional! 5.0/5
                                                                    (14 reviews)
                                                                    avg/night
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 9
                                                                    Cottage #411385vb
                                                                    14
                                                                    Viewed 31 times in the last 48 hours
                                                                      Wonderful! 4.9/5
                                                                      (16 reviews)
                                                                      avg/night
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 8
                                                                      House #168407
                                                                      16
                                                                      Viewed 31 times in the last 48 hours
                                                                        • 4 BR
                                                                        • 2 BA
                                                                        • Sleeps 8
                                                                        House #3917327
                                                                        0
                                                                        Viewed 18 times in the last 48 hours
                                                                          Wonderful! 4.8/5
                                                                          (37 reviews)
                                                                          avg/night
                                                                          • 2 BR
                                                                          • 2 BA
                                                                          • Sleeps 6
                                                                          Cottage #60379vb
                                                                          37
                                                                          Viewed 17 times in the last 48 hours
                                                                            Wonderful! 4.9/5
                                                                            (13 reviews)
                                                                            avg/night
                                                                            • 4 BR
                                                                            • 2 BA
                                                                            • Separate Toilet
                                                                            • Sleeps 10
                                                                            House #682992vb
                                                                            13
                                                                            Viewed 13 times in the last 48 hours
                                                                              Wonderful! 4.9/5
                                                                              (11 reviews)
                                                                              avg/night
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 6
                                                                              Cottage #327380vb
                                                                              11
                                                                              Viewed 15 times in the last 48 hours
                                                                                avg/night
                                                                                • 4 BR
                                                                                • 3 BA
                                                                                • Separate Toilet
                                                                                • Sleeps 9
                                                                                House #961695
                                                                                3
                                                                                Viewed 78 times in the last 48 hours
                                                                                  Very Good! 4.2/5
                                                                                  (5 reviews)
                                                                                  avg/night
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                  Cottage #7002952
                                                                                  5
                                                                                  Viewed 16 times in the last 48 hours
                                                                                    Wonderful! 4.9/5
                                                                                    (16 reviews)
                                                                                    avg/night
                                                                                    • 3 BR
                                                                                    • 5 BA
                                                                                    • Sleeps 6
                                                                                    Farmhouse #305432vb
                                                                                    16
                                                                                    Viewed 13 times in the last 48 hours
                                                                                      Exceptional! 5.0/5
                                                                                      (5 reviews)
                                                                                      avg/night
                                                                                      • 3 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 6
                                                                                      Cabin #721143vb
                                                                                      5
                                                                                      Viewed 14 times in the last 48 hours
                                                                                        avg/night
                                                                                        • 3 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 6
                                                                                        House #769188vb
                                                                                        2
                                                                                        Viewed 15 times in the last 48 hours
                                                                                          • 4 BR
                                                                                          • 3 BA
                                                                                          • Sleeps 8
                                                                                          House #292678vb
                                                                                          1
                                                                                          Viewed 23 times in the last 48 hours
                                                                                            Exceptional! 5.0/5
                                                                                            (10 reviews)
                                                                                            avg/night
                                                                                            • 5 BR
                                                                                            • 3 BA
                                                                                            • Separate Toilet
                                                                                            • Sleeps 18
                                                                                            House #429253vb
                                                                                            10
                                                                                            Viewed 44 times in the last 48 hours
                                                                                              Excellent! 4.6/5
                                                                                              (9 reviews)
                                                                                              avg/night
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 6
                                                                                              House #612581vb
                                                                                              9
                                                                                              Viewed 6 times in the last 48 hours
                                                                                                avg/night
                                                                                                • 6 BR
                                                                                                • 4 BA
                                                                                                • Sleeps 14
                                                                                                Estate #4200107
                                                                                                1
                                                                                                Viewed 23 times in the last 48 hours
                                                                                                  Exceptional! 5.0/5
                                                                                                  (5 reviews)
                                                                                                  avg/night
                                                                                                  • 5 BR
                                                                                                  • 3 BA
                                                                                                  • Separate Toilet
                                                                                                  • Sleeps 10
                                                                                                  Chateau / Country House #4147861
                                                                                                  5
                                                                                                  Viewed 31 times in the last 48 hours
                                                                                                    Exceptional! 5.0/5
                                                                                                    (5 reviews)
                                                                                                    avg/night
                                                                                                    • 4 BR
                                                                                                    • 2 BA
                                                                                                    • Separate Toilet
                                                                                                    • Sleeps 13
                                                                                                    House #232799vb
                                                                                                    5
                                                                                                    Viewed 23 times in the last 48 hours
                                                                                                      Exceptional! 5.0/5
                                                                                                      (30 reviews)
                                                                                                      avg/night
                                                                                                      • 5 BR
                                                                                                      • 3 BA
                                                                                                      • Separate Toilet
                                                                                                      • Sleeps 11
                                                                                                      House #414495vb
                                                                                                      30
                                                                                                      Viewed 23 times in the last 48 hours
                                                                                                      • 1 - 50 of 76