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

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.

Use filters to narrow your search results!

Chesapeake Bay Holiday Homes & Cottages (409)

  • 1 - 50 of 409
Additional service fee may apply.
    • 2 BR
    • 1 BA
    • Sleeps 4
    18
      • 2 BR
      • 1 BA
      • Sleeps 4
      3
        • 2 BR
        • 1 BA
        • Separate Toilet
        • Sleeps 4
        16
          • 1 BR
          • 1 BA
          • Sleeps 3
          34
            • 2 BR
            • 1 BA
            • Separate Toilet
            • Sleeps 5
            20
              • 2 BR
              • 1 BA
              • Sleeps 5
              34
                • 1 BR
                • 1 BA
                • Sleeps 2
                50
                  • 6 BR
                  • 3 BA
                  • Separate Toilet
                  • Sleeps 14
                  22
                    • 3 BR
                    • 2 BA
                    • Separate Toilet
                    • Sleeps 9
                    17
                      • 7 BR
                      • 6 BA
                      • Separate Toilet
                      • Sleeps 28
                      15
                        • 1 BR
                        • 1 BA
                        • Sleeps 3
                        15
                          • 1 BR
                          • 1 BA
                          • Sleeps 5
                          24
                            • 2 BR
                            • 1 BA
                            • Sleeps 4
                            10
                              • 3 BR
                              • 2 BA
                              • Sleeps 8
                              5
                                • 2 BR
                                • 3 BA
                                • Sleeps 6
                                17
                                  • 5 BR
                                  • 5 BA
                                  • Sleeps 12
                                  8
                                    • 2 BR
                                    • 2 BA
                                    • Sleeps 6
                                    15
                                      NEW!
                                      • 2 BR
                                      • 1 BA
                                      • Separate Toilets
                                      • Sleeps 5
                                      4
                                        • 4 BR
                                        • 5 BA
                                        • Sleeps 10
                                        20
                                          • 3 BR
                                          • 3 BA
                                          • Sleeps 8
                                          36
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 6
                                            17
                                              • 2 BR
                                              • 1 BA
                                              • Separate Toilet
                                              • Sleeps 5
                                              23
                                                • 4 BR
                                                • 2 BA
                                                • Sleeps 10
                                                7
                                                  • 5 BR
                                                  • 2 BA
                                                  • Sleeps 12
                                                  21
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 3
                                                    37
                                                      NEW!
                                                      • 4 BR
                                                      • 3 BA
                                                      • Sleeps 10
                                                      6
                                                        • 5 BR
                                                        • 5 BA
                                                        • Sleeps 12
                                                        31
                                                          • 3 BR
                                                          • 3 BA
                                                          • Separate Toilet
                                                          • Sleeps 9
                                                          12
                                                            • 2 BR
                                                            • 1 BA
                                                            • Sleeps 4
                                                            33
                                                              • 4 BR
                                                              • 4 BA
                                                              • Sleeps 10
                                                              31
                                                                • 6 BR
                                                                • 3 BA
                                                                • Sleeps 13
                                                                5
                                                                  • 5 BR
                                                                  • 3 BA
                                                                  • Sleeps 12
                                                                  18
                                                                    • 4 BR
                                                                    • 2 BA
                                                                    • Sleeps 11
                                                                    5
                                                                      • 2 BR
                                                                      • 2 BA
                                                                      • Separate Toilet
                                                                      • Sleeps 12
                                                                      30
                                                                        • 2 BR
                                                                        • 2 BA
                                                                        • Sleeps 6
                                                                        9
                                                                          • 2 BR
                                                                          • 1 BA
                                                                          • Sleeps 4
                                                                          20
                                                                            • 3 BR
                                                                            • 2 BA
                                                                            • Sleeps 6
                                                                            33
                                                                              • 2 BR
                                                                              • 1 BA
                                                                              • Sleeps 5
                                                                              5
                                                                                • 4 BR
                                                                                • 2 BA
                                                                                • Separate Toilet
                                                                                • Sleeps 10
                                                                                6
                                                                                  • 4 BR
                                                                                  • 4 BA
                                                                                  • Separate Toilet
                                                                                  • Sleeps 11
                                                                                  41
                                                                                    • 2 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 5
                                                                                    14
                                                                                      • 1 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 5
                                                                                      26
                                                                                        NEW!
                                                                                        • 3 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 6
                                                                                        6
                                                                                          NEW!
                                                                                          • 3 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 6
                                                                                          5
                                                                                            • 3 BR
                                                                                            • 2 BA
                                                                                            • Separate Toilet
                                                                                            • Sleeps 8
                                                                                            15
                                                                                              NEW!
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 8
                                                                                              5
                                                                                                • 1 BR
                                                                                                • Separate Toilet
                                                                                                • Sleeps 2
                                                                                                8
                                                                                                  • 2 BR
                                                                                                  • 1 BA
                                                                                                  • Separate Toilet
                                                                                                  • Sleeps 6
                                                                                                  22
                                                                                                    • 5 BR
                                                                                                    • 4 BA
                                                                                                    • Sleeps 12
                                                                                                    2 Reviews
                                                                                                      NEW!
                                                                                                      • 1 BR
                                                                                                      • 1 BA
                                                                                                      • Separate Toilet
                                                                                                      • Sleeps 4
                                                                                                      3
                                                                                                      • 1 - 50 of 409