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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.

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Chesapeake Bay Holiday Homes & Cottages (300+)

  • 1 - 50 of 300+
Additional service fee may apply.
    Wonderful! 4.8/5
    (39 reviews)
    avg/night
    • 1 BR
    • 1 BA
    • Sleeps 3
    Cottage #470232vb
    39
      Exceptional! 5.0/5
      (41 reviews)
      avg/night
      • 2 BR
      • 2 BA
      • Sleeps 6
      House #626793vb
      41
      Viewed 18 times in the last 48 hours
        Wonderful! 4.8/5
        (20 reviews)
        avg/night
        • 2 BR
        • 3 BA
        • Sleeps 6
        Cottage #705054vb
        20
        Viewed 16 times in the last 48 hours
          Wonderful! 4.9/5
          (44 reviews)
          avg/night
          • 4 BR
          • 4 BA
          • Separate Toilet
          • Sleeps 11
          House #394464vb
          44
          Viewed 20 times in the last 48 hours
            Wonderful! 4.8/5
            (23 reviews)
            avg/night
            • 4 BR
            • 5 BA
            • Sleeps 10
            Cottage #500065vb
            23
            Viewed 16 times in the last 48 hours
              Wonderful! 4.9/5
              (24 reviews)
              avg/night
              • 6 BR
              • 3 BA
              • Separate Toilet
              • Sleeps 14
              Estate #701079vb
              24
              Viewed 24 times in the last 48 hours
                Excellent! 4.7/5
                (17 reviews)
                avg/night
                • 3 BR
                • 2 BA
                • Separate Toilet
                • Sleeps 9
                Estate #3021814
                17
                Viewed 9 times in the last 48 hours
                  Exceptional! 5.0/5
                  (16 reviews)
                  avg/night
                  • 7 BR
                  • 6 BA
                  • Separate Toilet
                  • Sleeps 28
                  Estate #409548vb
                  16
                  Viewed 25 times in the last 48 hours
                    Exceptional! 5.0/5
                    (7 reviews)
                    avg/night
                    • 1 BR
                    • 2 BA
                    • Sleeps 5
                    Cabin #4178435
                    7
                    Viewed 18 times in the last 48 hours
                      Excellent! 4.7/5
                      (19 reviews)
                      avg/night
                      • 1 BR
                      • 1 BA
                      • Sleeps 3
                      Cottage #766952vb
                      19
                      Viewed 31 times in the last 48 hours
                        Exceptional! 5.0/5
                        (31 reviews)
                        avg/night
                        • 2 BR
                        • 1 BA
                        • Sleeps 4
                        Cottage #820614vb
                        31
                        Viewed 34 times in the last 48 hours
                          Exceptional! 5.0/5
                          (34 reviews)
                          avg/night
                          • 5 BR
                          • 5 BA
                          • Sleeps 12
                          House #208680vb
                          34
                          Viewed 21 times in the last 48 hours
                            Exceptional! 5.0/5
                            (20 reviews)
                            avg/night
                            • 7 BR
                            • 5 BA
                            • Separate Toilet
                            • Sleeps 14
                            House #609538vb
                            20
                            Viewed 25 times in the last 48 hours
                              Wonderful! 4.8/5
                              (5 reviews)
                              avg/night
                              • 2 BR
                              • 1 BA
                              • Sleeps 4
                              Condo #681807vb
                              5
                                Excellent! 4.5/5
                                (23 reviews)
                                avg/night
                                • 5 BR
                                • 2 BA
                                • Sleeps 12
                                House #358885vb
                                23
                                Viewed 9 times in the last 48 hours
                                  Exceptional! 5.0/5
                                  (5 reviews)
                                  avg/night
                                  • 5 BR
                                  • 3 BA
                                  • Separate Toilet
                                  • Sleeps 12
                                  House #805100vb
                                  5
                                  Viewed 21 times in the last 48 hours
                                    Wonderful! 4.8/5
                                    (21 reviews)
                                    avg/night
                                    • 2 BR
                                    • 1 BA
                                    • Separate Toilet
                                    • Sleeps 4
                                    Cottage #599767vb
                                    21
                                    Viewed 9 times in the last 48 hours
                                      Excellent! 4.7/5
                                      (39 reviews)
                                      avg/night
                                      • 1 BR
                                      • 1 BA
                                      • Sleeps 3
                                      Cottage #908053
                                      39
                                      Viewed 5 times in the last 48 hours
                                        • 3 BR
                                        • 2 BA
                                        • Sleeps 7
                                        House #408472vb
                                        37
                                          Wonderful! 4.8/5
                                          (36 reviews)
                                          avg/night
                                          • 2 BR
                                          • 1 BA
                                          • Sleeps 5
                                          House #7080944
                                          36
                                          Viewed 20 times in the last 48 hours
                                            Wonderful! 4.9/5
                                            (16 reviews)
                                            avg/night
                                            • 5 BR
                                            • 4 BA
                                            • Sleeps 18
                                            House #581725vb
                                            16
                                            Viewed 19 times in the last 48 hours
                                              Wonderful! 4.9/5
                                              (17 reviews)
                                              avg/night
                                              • 3 BR
                                              • 2 BA
                                              • Separate Toilet
                                              • Sleeps 6
                                              Cottage #482154vb
                                              17
                                              Viewed 6 times in the last 48 hours
                                                Wonderful! 4.8/5
                                                (40 reviews)
                                                avg/night
                                                • 4 BR
                                                • 3 BA
                                                • Sleeps 10
                                                House #40646vb
                                                40
                                                Viewed 24 times in the last 48 hours
                                                  Exceptional! 5.0/5
                                                  (9 reviews)
                                                  avg/night
                                                  • 4 BR
                                                  • 2 BA
                                                  • Separate Toilet
                                                  • Sleeps 10
                                                  House #803091vb
                                                  9
                                                  Viewed 26 times in the last 48 hours
                                                    • 2 BR
                                                    • 2 BA
                                                    • Separate Toilets
                                                    • Sleeps 6
                                                    House #169544
                                                    6
                                                      Wonderful! 4.9/5
                                                      (39 reviews)
                                                      avg/night
                                                      • 6 BR
                                                      • 6 BA
                                                      • Sleeps 15
                                                      Estate #476899vb
                                                      39
                                                      Viewed 12 times in the last 48 hours
                                                        Wonderful! 4.9/5
                                                        (58 reviews)
                                                        avg/night
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 8
                                                        Cabin #556055vb
                                                        58
                                                        Viewed 16 times in the last 48 hours
                                                          Exceptional! 5.0/5
                                                          (32 reviews)
                                                          avg/night
                                                          • 2 BR
                                                          • 2 BA
                                                          • Separate Toilet
                                                          • Sleeps 12
                                                          House #465337vb
                                                          32
                                                          Viewed 16 times in the last 48 hours
                                                            Exceptional! 5.0/5
                                                            (35 reviews)
                                                            avg/night
                                                            • 4 BR
                                                            • 1 BA
                                                            • Separate Toilet
                                                            • Sleeps 8
                                                            Cottage #450640vb
                                                            35
                                                            Viewed 23 times in the last 48 hours
                                                              Wonderful! 4.9/5
                                                              (11 reviews)
                                                              avg/night
                                                              • 5 BR
                                                              • 5 BA
                                                              • Sleeps 12
                                                              House #759930vb
                                                              11
                                                              Viewed 7 times in the last 48 hours
                                                                Wonderful! 4.9/5
                                                                (57 reviews)
                                                                avg/night
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 2
                                                                Cottage #61400vb
                                                                57
                                                                Viewed 15 times in the last 48 hours
                                                                  Wonderful! 4.8/5
                                                                  (35 reviews)
                                                                  avg/night
                                                                  • 2 BR
                                                                  • 1 BA
                                                                  • Sleeps 4
                                                                  House #512727vb
                                                                  35
                                                                  Viewed 6 times in the last 48 hours
                                                                    Exceptional! 5.0/5
                                                                    (23 reviews)
                                                                    avg/night
                                                                    • 2 BR
                                                                    • 1 BA
                                                                    • Sleeps 5
                                                                    House #986821
                                                                    23
                                                                    Viewed 11 times in the last 48 hours
                                                                      Wonderful! 4.8/5
                                                                      (13 reviews)
                                                                      avg/night
                                                                      • 2 BR
                                                                      • 1 BA
                                                                      • Sleeps 4
                                                                      Cottage #4144472
                                                                      13
                                                                        Exceptional! 5.0/5
                                                                        (41 reviews)
                                                                        avg/night
                                                                        • 3 BR
                                                                        • 3 BA
                                                                        • Sleeps 8
                                                                        House #294688vb
                                                                        41
                                                                        Viewed 15 times in the last 48 hours
                                                                          Excellent! 4.4/5
                                                                          (28 reviews)
                                                                          avg/night
                                                                          • 6 BR
                                                                          • 3 BA
                                                                          • Separate Toilet
                                                                          • Sleeps 9
                                                                          House #198445vb
                                                                          28
                                                                          Viewed 29 times in the last 48 hours
                                                                            Wonderful! 4.9/5
                                                                            (64 reviews)
                                                                            avg/night
                                                                            • 4 BR
                                                                            • 4 BA
                                                                            • Sleeps 8
                                                                            House #432739vb
                                                                            64
                                                                            Viewed 18 times in the last 48 hours
                                                                              Excellent! 4.7/5
                                                                              (44 reviews)
                                                                              avg/night
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 10
                                                                              House #252098vb
                                                                              44
                                                                                Exceptional! 5.0/5
                                                                                (25 reviews)
                                                                                avg/night
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 5
                                                                                Cottage #371261vb
                                                                                25
                                                                                Viewed 9 times in the last 48 hours
                                                                                  • 5 BR
                                                                                  • 3 BA
                                                                                  • Separate Toilet
                                                                                  • Sleeps 12
                                                                                  House #512993vb
                                                                                  30
                                                                                    Wonderful! 4.8/5
                                                                                    (39 reviews)
                                                                                    avg/night
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 6
                                                                                    Condo #357989vb
                                                                                    39
                                                                                    Viewed 18 times in the last 48 hours
                                                                                      Excellent! 4.5/5
                                                                                      (13 reviews)
                                                                                      avg/night
                                                                                      • 4 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 10
                                                                                      House #3771110
                                                                                      13
                                                                                      Viewed 26 times in the last 48 hours
                                                                                        • 5 BR
                                                                                        • 3 BA
                                                                                        • Sleeps 15
                                                                                        Farmhouse #663105vb
                                                                                        11
                                                                                          Wonderful! 4.9/5
                                                                                          (7 reviews)
                                                                                          avg/night
                                                                                          • 6 BR
                                                                                          • 4 BA
                                                                                          • Separate Toilets
                                                                                          • Sleeps 14
                                                                                          House #3926292
                                                                                          7
                                                                                          Viewed 15 times in the last 48 hours
                                                                                            Wonderful! 4.8/5
                                                                                            (21 reviews)
                                                                                            avg/night
                                                                                            • 2 BR
                                                                                            • 1 BA
                                                                                            • Separate Toilet
                                                                                            • Sleeps 5
                                                                                            Cottage #359766vb
                                                                                            21
                                                                                            Viewed 24 times in the last 48 hours
                                                                                              Wonderful! 4.9/5
                                                                                              (21 reviews)
                                                                                              avg/night
                                                                                              • 5 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 12
                                                                                              House #585277vb
                                                                                              21
                                                                                              Viewed 12 times in the last 48 hours
                                                                                                Wonderful! 4.9/5
                                                                                                (14 reviews)
                                                                                                avg/night
                                                                                                • 5 BR
                                                                                                • 5 BA
                                                                                                • Sleeps 10
                                                                                                Lodge #3920901
                                                                                                14
                                                                                                Viewed 16 times in the last 48 hours
                                                                                                  Excellent! 4.7/5
                                                                                                  (15 reviews)
                                                                                                  avg/night
                                                                                                  • 4 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 10
                                                                                                  House #704799vb
                                                                                                  15
                                                                                                  Viewed 20 times in the last 48 hours
                                                                                                    • 2 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 6
                                                                                                    House #702464vb
                                                                                                    11
                                                                                                      Wonderful! 4.9/5
                                                                                                      (10 reviews)
                                                                                                      avg/night
                                                                                                      • 3 BR
                                                                                                      • 1 BA
                                                                                                      • Separate Toilet
                                                                                                      • Sleeps 10
                                                                                                      Cottage #738202vb
                                                                                                      10
                                                                                                      Viewed 9 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+