St. Leonard Rentals

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16 Houses

(1) Excellent 

    24

    New! Beachfront 4BR St. Leonard Cottage w/ Deck!

    Calvert County / St. Leonard

    Saint Leonard cottage

    4 8 2 nights min

    • 4 bedrooms
    • sleeps 8
    • 2 nights min
    • Child Friendly
    • Air conditioning

    Price per night from

    $189

    Responds fast!
    avg. 9 minutes

    Price per night from

    $189

      10

      Harbor Cottage at the Chesapeake Bay

      Calvert County / St. Leonard

      Saint Leonard cottage

      2 6 3 nights min

      • 2 bedrooms
      • sleeps 6
      • 3 nights min
      • Beach / lakeside relaxation
      • Child Friendly
      • Air conditioning

      Price per night from

      $306

      Price per night from

      $306

        24

        St. Leonard Cottage w/Pool Overlooking Wells Cove!

        Calvert County / St. Leonard

        Saint Leonard cottage

        1 2 2 nights min

        • 1 bedroom
        • sleeps 2
        • 2 nights min
        • Swimming pool
        • Child Friendly
        • Air conditioning

        Price per night from

        $106

        Responds fast!
        avg. 9 minutes

        Price per night from

        $106

        Great rentals within 20 miles that match your search

        Distance approx 18.7 km from St. Leonard

        (4) Excellent 

          20

          Best kept secret by the bay (Entire House)

          Maryland / Fishing Creek

          Fishing Creek house

          3 4 3 nights min

          • 3 bedrooms
          • sleeps 4
          • 3 nights min
          • Air conditioning
          • Private garden

          Price per night from

          $199

          Responds fast!
          avg. 3 hours 10 minutes

          Price per night from

          $199

          Distance approx 10.12 km from St. Leonard

            24

            Chesapeake Beach Apt. Walk to Bay, Beach & Marina!

            Calvert County / Chesapeake Beach

            Chesapeake Beach apartment

            1 4 min stay varies

            • 1 bedroom
            • sleeps 4
            • min stay varies
            • Air conditioning

            Price per night from

            $83

            Responds fast!
            avg. 9 minutes

            Price per night from

            $83

            Distance approx 15.83 km from St. Leonard

            (5) Very Good 

              17

              Seahorse Guest Cottage near the Bay, dog friendly

              Calvert County / North Beach

              North Beach cottage

              1 5 2 nights min

              • 1 bedroom
              • sleeps 5
              • 2 nights min
              • Beach / lakeside relaxation
              • Nearest beach 0.2 mi
              • Child Friendly

              Price per night from

              $189

              Responds fast!
              avg. 1 hour 32 minutes

              Price per night from

              $189

              Distance approx 18.22 km from St. Leonard

              (2) Very Good 

                35

                Chesapeake Bay Waterfront on Hoopers Island with Private Beach

                Maryland / Fishing Creek

                Fishing Creek house

                5 12 min stay varies

                • 5 bedrooms
                • sleeps 12
                • min stay varies
                • Child Friendly
                • Air conditioning
                • Pet Friendly

                Price per night from

                $236

                Price per night from

                $236

                Distance approx 17.42 km from St. Leonard

                  11

                  Panoramic Views of Herrington Harbour on the Bay.

                  Calvert County / North Beach

                  North Beach house

                  3 8 1 night min

                  • 3 bedrooms
                  • sleeps 8
                  • 1 night min
                  • Child Friendly
                  • Air conditioning
                  • Pet Friendly

                  Price per night from

                  $589

                  Price per night from

                  $589

                  Distance approx 16.22 km from St. Leonard

                    9

                    Renovated Luxury Waterview House

                    Calvert County / North Beach

                    North Beach house

                    3 6 2 nights min

                    • 3 bedrooms
                    • sleeps 6
                    • 2 nights min
                    • Child Friendly

                    Price per night from

                    $353

                    Price per night from

                    $353

                    Distance approx 4.03 km from St. Leonard Show on Map

                      10

                      Business or Leisure?

                      Calvert County / Lusby

                      Lusby guest house

                      1 4 2 nights min

                      • 1 bedroom
                      • sleeps 4
                      • 2 nights min
                      • Child Friendly
                      • Air conditioning

                      Price per night from

                      $77

                      Responds fast!
                      avg. 3 hours 20 minutes

                      Price per night from

                      $77

                      Distance approx 18.51 km from St. Leonard

                      (4) Excellent 

                        38

                        Hoopers Island Studio, 360 Degrees WATER VIEWS

                        Maryland / Fishing Creek

                        Fishing Creek apartment

                        1 3 min stay varies

                        • 1 bedroom
                        • sleeps 3
                        • min stay varies
                        • Beach / lakeside relaxation
                        • Nearest beach 32 mi
                        • Ask about children
                        “What a fantastic stay!” As soon as we stepped out of our car, we felt like we hit the jackpot. The views in front and in back of the house are breathtaking, with water stretching to the horizons. Inside the house, we found all that we could need and
                        …see more

                        Price per night from

                        $189

                        Responds fast!
                        avg. 1 hour 25 minutes

                        Price per night from

                        $189

                        Distance approx 16.16 km from St. Leonard

                        (12) Very Good 

                          31

                          Stunning, Newer Chesapeake Waterfront Estate, Pool - 6/7 Bedrms 5 Baths

                          Maryland / Cambridge

                          Cambridge house

                          6 20 min stay varies

                          • 6 bedrooms
                          • sleeps 20
                          • min stay varies
                          • Beach / lakeside relaxation
                          • Nearest beach 0.1 mi
                          • Swimming pool
                          “Outstanding Vacation Rental” Our extended family (22 people - 13A/9K) had a great week at Saddle Beach. The house was beautiful and in very good condition. The option of being in the pool or the river during the day was wonderful. The house was cle
                          …see more

                          Price per night from

                          $587

                          Price per night from

                          $587

                          Distance approx 18.85 km from St. Leonard

                            9

                            Eastern Shore Waterfront Home, Ready for Spring and Summer!

                            Maryland / Fishing Creek

                            Fishing Creek house

                            3 10 3 nights min

                            • 3 bedrooms
                            • sleeps 10
                            • 3 nights min
                            • Beach / lakeside relaxation
                            • Child Friendly
                            • Air conditioning

                            Price per night from

                            $265

                            Price per night from

                            $265

                            Distance approx 16.16 km from St. Leonard

                              17

                              Deerpond Carriage House

                              Maryland / Woolford

                              Woolford guest house

                              1 2 3 nights min

                              • 1 bedroom
                              • sleeps 2
                              • 3 nights min
                              • Swimming pool
                              • Air conditioning
                              • Private garden

                              Price per night from

                              $206

                              Price per night from

                              $206

                              Distance approx 17.1 km from St. Leonard

                              (15) Excellent 

                                35

                                Year Round Estate on Bay / Fam. Reunions / Slps 28

                                Maryland / Cambridge

                                Cambridge house

                                7 28 min stay varies

                                • 7 bedrooms
                                • sleeps 28
                                • min stay varies
                                • Beach / lakeside relaxation
                                • Swimming pool
                                • Ask about children
                                “Unbelievable Home in an Unbelievable Setting!!!” Our family cant thank you enough for the memories made at captains quarters this summer. This was the first time getting away with the entire family (kids grandkids, grand parents, etc) and it was prop
                                …see more

                                Price per night from

                                $1,028

                                Price per night from

                                $1,028

                                Distance approx 18.95 km from St. Leonard

                                (10) Excellent 

                                  50

                                  Cottage at Heron Cove, Chesapeake Bay, Cambridge

                                  Maryland / Cambridge

                                  Cambridge cottage

                                  3 5 min stay varies

                                  • 3 bedrooms
                                  • sleeps 5
                                  • min stay varies
                                  • Beach / lakeside relaxation
                                  • Child Friendly
                                  • Air conditioning

                                  Price per night from

                                  $173

                                  Price per night from

                                  $173