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
Cancel Clear Filters Apply Filters

Property Type

Booking Options

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Vacation Rentals in Chesapeake Bay, Maryland (351)

  • 1 - 50 of 351
Additional fees apply. Taxes may be added.
    • 2 BR
    • 1 BA
    • Sleeps 4
    Cottage #820614vb
      • 2 BR
      • 1 BA
      • 1 HF BA
      • Sleeps 4
      Cottage #599767vb
        • 2 BR
        • 1 BA
        • Sleeps 4
        Condo #681807vb
          • 1 BR
          • 1 BA
          • Sleeps 2
          Cottage #61400vb
            • 2 BR
            • 1 BA
            • 1 HF BA
            • Sleeps 5
            Cottage #359766vb
              • 1 BR
              • 1 BA
              • Sleeps 3
              Cottage #766952vb
                • 2 BR
                • 3 BA
                • Sleeps 6
                Cottage #705054vb
                  • 1 BR
                  • 1 BA
                  • Sleeps 3
                  Cottage #908053
                    • 2 BR
                    • 1 BA
                    • Sleeps 5
                    House #7080944
                      • 2 BR
                      • 1 BA
                      • 1 HF BA
                      • Sleeps 5
                      Cottage #229963vb
                        • 2 BR
                        • 1 BA
                        • 2 HF BA
                        • Sleeps 5
                        Cottage #844888vb
                          • 4 BR
                          • 4 BA
                          • 1 HF BA
                          • Sleeps 11
                          House #394464vb
                            • 3 BR
                            • 2 BA
                            • Sleeps 8
                            House #3944507
                              • 1 BR
                              • 1 BA
                              • Sleeps 5
                              Cottage #371261vb
                                • 2 BR
                                • 2 BA
                                • 1 HF BA
                                • Sleeps 12
                                House #465337vb
                                  • 4 BR
                                  • 5 BA
                                  • Sleeps 10
                                  Cottage #500065vb
                                    • 5 BR
                                    • 5 BA
                                    • Sleeps 12
                                    House #759930vb
                                      • 2 BR
                                      • 1 BA
                                      • Sleeps 4
                                      Cottage #4144472
                                        • 5 BR
                                        • 2 BA
                                        • Sleeps 12
                                        House #358885vb
                                          • 3 BR
                                          • 3 BA
                                          • Sleeps 8
                                          House #294688vb
                                            • 2 BR
                                            • 2 BA
                                            • Sleeps 6
                                            Cottage #644681vb
                                              • 3 BR
                                              • 2 BA
                                              • Sleeps 6
                                              Cottage #4230519
                                                • 2 BR
                                                • 2 BA
                                                • Sleeps 5
                                                Cottage #608459vb
                                                  • 5 BR
                                                  • 5 BA
                                                  • Sleeps 12
                                                  House #208680vb
                                                    • 2 BR
                                                    • 1 BA
                                                    • Sleeps 4
                                                    House #512727vb
                                                      • 1 BR
                                                      • 1 BA
                                                      • Sleeps 3
                                                      Cottage #470232vb
                                                        • 2 BR
                                                        • 1 BA
                                                        • Sleeps 5
                                                        Apartment #481330vb
                                                          • 2 BR
                                                          • Sleeps 4
                                                          Apartment #606172vb
                                                            • 2 BR
                                                            • 1 BA
                                                            • Sleeps 4
                                                            Condo #571558vb
                                                              • 3 BR
                                                              • 2 BA
                                                              • Sleeps 6
                                                              Condo #357989vb
                                                                • 1 BR
                                                                • 1 BA
                                                                • 1 HF BA
                                                                • Sleeps 4
                                                                Apartment #844031vb
                                                                  • 2 BR
                                                                  • 2 BA
                                                                  • Sleeps 6
                                                                  Condo #774655vb
                                                                    • 3 BR
                                                                    • 3 BA
                                                                    • 1 HF BA
                                                                    • Sleeps 9
                                                                    House #572361vb
                                                                      • 2 BR
                                                                      • 1 BA
                                                                      • Sleeps 5
                                                                      House #7082746
                                                                        • 3 BR
                                                                        • 3 BA
                                                                        • Sleeps 9
                                                                        House #7092687
                                                                          • 1 BR
                                                                          • 2 BA
                                                                          • Sleeps 5
                                                                          Cabin #4178435
                                                                            • 4 BR
                                                                            • 2 BA
                                                                            • Sleeps 11
                                                                            House #743272vb
                                                                              • 4 BR
                                                                              • 2 BA
                                                                              • Sleeps 10
                                                                              House #398147vb
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • 1 HF BA
                                                                                • Sleeps 8
                                                                                Cottage #503705vb
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                  House #759063vb
                                                                                    • 4 BR
                                                                                    • 3 BA
                                                                                    • Sleeps 8
                                                                                    House #684953vb
                                                                                      • 5 BR
                                                                                      • 5 BA
                                                                                      • Sleeps 10
                                                                                      Lodge #3920901
                                                                                        • 1 BR
                                                                                        • 1 BA
                                                                                        • 1 HF BA
                                                                                        • Sleeps 4
                                                                                        Cottage #429271vb
                                                                                          • 6 BR
                                                                                          • 3 BA
                                                                                          • Sleeps 13
                                                                                          House #739289vb
                                                                                            • 5 BR
                                                                                            • 3 BA
                                                                                            • Sleeps 12
                                                                                            House #585277vb
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 5
                                                                                              House #833209vb
                                                                                                • 4 BR
                                                                                                • 2 BA
                                                                                                • 1 HF BA
                                                                                                • Sleeps 10
                                                                                                House #803091vb
                                                                                                  • 2 BR
                                                                                                  • 1 BA
                                                                                                  • 1 HF BA
                                                                                                  • Sleeps 6
                                                                                                  House #431733vb
                                                                                                    • 1 BR
                                                                                                    • 1 HF BA
                                                                                                    • Sleeps 2
                                                                                                    Cottage #3251603
                                                                                                      • 2 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 5
                                                                                                      House #986821
                                                                                                      • 1 - 50 of 351